KR940005626A - 항생 화합물 - Google Patents
항생 화합물 Download PDFInfo
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- KR940005626A KR940005626A KR1019930004664A KR930004664A KR940005626A KR 940005626 A KR940005626 A KR 940005626A KR 1019930004664 A KR1019930004664 A KR 1019930004664A KR 930004664 A KR930004664 A KR 930004664A KR 940005626 A KR940005626 A KR 940005626A
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- methylcarbapenem
- ylthio
- hydroxyethyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract 16
- 230000003115 biocidal effect Effects 0.000 title 1
- -1 benzamidosulfonyl Chemical group 0.000 claims abstract 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 6
- 239000001257 hydrogen Substances 0.000 claims abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 6
- 150000003839 salts Chemical class 0.000 claims abstract 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims abstract 3
- 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 claims abstract 2
- DIORMHZUUKOISG-UHFFFAOYSA-N sulfoformic acid Chemical compound OC(=O)S(O)(=O)=O DIORMHZUUKOISG-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000006239 protecting group Chemical group 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 3
- 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
- 125000001475 halogen functional 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
- WLMAZNVZKJEDEM-VKFRQQTDSA-N CC1[C@@H]2C(C(=O)N2C(=C1SC3CC(NC3)C(=O)NC4=C(C=CC(=C4)S(=O)(=O)O)O)C(=O)O)C(C)O Chemical compound CC1[C@@H]2C(C(=O)N2C(=C1SC3CC(NC3)C(=O)NC4=C(C=CC(=C4)S(=O)(=O)O)O)C(=O)O)C(C)O WLMAZNVZKJEDEM-VKFRQQTDSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 125000005236 alkanoylamino group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003118 aryl 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
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000004986 diarylamino group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 229940041011 carbapenems Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 229940124597 therapeutic agent Drugs 0.000 abstract 1
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- 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
-
- 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
- C07D207/04—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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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- 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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- 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
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- 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
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Abstract
본 발명은 하기 일반식(I)의 화합물 또는 이의 약학적으로 허용가능한 염 또는 이의 생체내 가수분해성 에스테르에 관한 것이다.
상기 식에서, R1은 1-히드록시에틸, 1-플루오로에틸 또는 히드록시메틸이고; R2는 수소 또는 Cl-4알킬이고; R3는 수소 또는 Cl-4알킬이고; P는 하기 일반식 (IA), (IB)또는 (IC)이며, 일반식(IB)에서의 나프틸기는 각 고리에서 결합되어 있는 카르바모일기의 질소에 결합될 수 있으며; Z는 카르복시, 설폰산, 설핀산, Cl-4알칸아 미도설포닐 (-SO2NHCOC1-3알킬), 벤즈아미도설포닐, Cl-4알킬설포닐카르바모일 (-CONHSO2Cl-4알킬), 페닐설포닐카르바모일, Cl-4알콕시카르바모일, 히드록시카르바모일, 설포아미노,Cl-4알칸설폰아미도, 시아노카르바모일, 시아노설파모일, 테트라졸-5-일, 3-히드록시이소옥사졸-4-일 및 3-히드록시이소옥사졸-5-일이며; P가 일반식(IA)또는 (IC)의 고리일때, Z는 카르복시가 아닐 경우에만 P는 임의로 치환된다. 또한, 본 발명의 화합물의 제조 방법, 이의 제조에서의 중간물질, 치료제로서의 이의 사용 및 이를 함유하는 약학적 조성물을 설명한다.
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 Cl-4알킬이고; R3는 수소 또는 Cl-4알킬이고; P는 하기 일반식 (IA), (IB)또는 (IC)이며, 일반식(IB)에서의 나프틸기는 각 고리에서 결합되어 있는 카르바모일기의 질소에 결합될 수 있으며; Z는 카르복시, 설폰산, 설핀산, Cl-4알칸아 미도설포닐 (-SO2NHCOC1-3알킬), 벤즈아미도설포닐, Cl-4알킬설포닐카르바모일 (-CONHSO2Cl-4알킬), 페닐설포닐카르바모일, Cl-4알콕시카르바모일, 히드록시카르바모일, 설포아미노,Cl-4알칸설폰아미도, 시아노카르바모일, 시아노설파모일, 테트라졸-5-일, 3-히드록시이소옥사졸-4-일 및 3-히드록시이소옥사졸-5-일이며; P는 할로, 시아노, Cl-4알킬, 니트로, 히드록시, 카르복시, Cl-4알콕시, 트리플루오로메틸, Cl-4알콕시카르보닐, 아미노, Cl-4알킬아미노, 디-Cl-4알킬아미노, 설폰산, Cl-4알킬 S(O)n-(이때, n은 0-2이다), Cl-4알카노일아미노, Cl-4알카노일(Cl-4알킬)아미노, 카르바모일, Cl-4알킬카르바모일 및 디-Cl-4알킬카르바모일로부터 선택되는 하나 또는 두개의 치환체로 부가로 치환될 수 있으며; 단, p가 일반식(IA) 또는 (IC)의 고리이고, Z가 설폰산 또는Cl-4알칸설폰아미도일때, 상기 고리는 카르복시로 치환되지 않으며; P가 일반식(IA) 또는 (IC)의 고리일때, Z는 카르복시가 아니다;
- 제1항에 있어서, R1이 1-히드록시에틸이고, R2가 메틸인 화합물.
- 제1항 또는 제2항에 있어서, 하기 일반식(Ⅳ)인 화합물.상기 식에서, P, R3및 P상의 임의의 치환체는 제1항에서 정의된 바와같다.
- 제3항에 있어서, 고리 P상의 치환체 Z가 설폰산, 테트라졸-5-일, Cl-4알킬설포닐카르바모일 또는 시아노카르바모일인 화합물.
- 제3항에 있어서, 고리 P상의 임의의 치환체가 할로, 시아노, Cl-4알킬, 니트로, 히드록시, Cl-4알콕시, 카르바모일, 아미노 및 트리플루오로메틸로부터 선택된 화합물.
- 제1항에 있어서, 하기와 같은 화합물 및 이의 약학적으로 허용가능한 염 (1R, 5S, 6S, 8R. 2'S, 4'S)-2-(2-(3-설포페닐카르바모일)피롤리딘-4-일티오)-6- (1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산; (1R, 5S, 6S, 8R, 2'S, 4'S)-2- (2-(3-메틸설포닐카르바모일페닐카르바모일)피롤리딘-4-일티오)-6-(1-히드톡시에틸)-1-메틸카르바페넴-3-카르복실산; (1R, 5S, 6S, 8R, 2'S, 4'S)-2-(2-(3-1H-테트라졸-5-일)페닐카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산; (1R, 5S, 6S, 8R, 2'S, 4'S)-2-(2-(2-히드록시-5-설포페닐카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산; (1R, 5S, 6S, 8R, 2'S, 4'S)-2-(2-(2-메록시-5-메틸--설포닐카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산; (1R, 5S, 6S, 8R, 2'S, 4'S)-2-(2-(3-페닐설포닐카르바모일페닐카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산, (1R, 5S, 6S, 8R, 2'S, 4'S)-2-(2-(2-메틸설포닐카르바모일-5-티에닐카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에 틸)-1-메틸카르바페넴-3-카르복실산; (1R, 5S, 6S, 8R, 2'S, 4'S)-2-(2-(2-시아노카르바모일-5-티에닐카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산:(1R, 5S, 6S, 8R, 2'S, 4'S)-2-(2-(2-설포-5- 티에닐카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산;(1R, 5S, 6S, 8R, 2'S, 4'S)-2-(2-(1-카르복시-3-나프틸카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산; (1R, 5S, 6S, 8R, 2'S, 4'S)-2-(2-(2-카르복시-3-나프틸카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸 )-1-메틸카르바페넴-3-카르복실산; (1R, 5S, 6S, 8R, 2'S, 4'S)-2-(2-(2-설포페닐카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산;또는 (1R, 5S, 6S, 8R, 2'S, 4'S)-(2-히드록시-4-설포-1-나프틸카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산.
- 제1항 내지 제6항중 어느 한 항에 따른 화합물 및 약제학적으로 허용가능한 담체를 포함하는 약학적 조성물.
- 하기 일반식(V)의 화합물을 탈보호시킨 후, 필요한 경우, (i)약학적으로 허용가능한 염을 형성시키고, (ii)이를 에스테르화시켜 생체내 가수분해성 에스테르를 형성시키는 것을 포함하는 화합물의 제조방법 :상기 식에서, R2는 제1항에서 정의된 바와같고; R10은 R3기(1항에서 정의된 바와같다) 또는 아미노 보호기이며; R13은 R1기(제1항에서 정의된 바와 같다), 보호된 히드록시메틸 또는 1-(보호된 히드록시)에틸기이며; R11은 수소 또는 카르복시 보호기이며; R12는 수소 또는 아미노 보호기이며; P1은 하기 일반식(ID), (IE) 또는 (IF)의 고리이며, 일반식(IE)에서의 나프틸기는 각 고리에서 결합되어 있는 카르바모일기의 질소에 결합될 수 있으며; R18은 Z기 또는 보호된 Z기이며, P1상의 임의의 치환체는 제1항에서 정의된 바와 같으며, 임의로 보호되며, 적어도 하나의 보호기가 존재한다 :
- 하기 (a)-(b)를 포함하고, 필요할 경우, (i)임의의 보호기의 제거; (ii)약학적으로 허용가능한 염의 형성; (iii)이를 에스테르화시킴으로써 생체내 가수분해성 에스테르를 형성시키는 제1항의 화합물 또는 제8항에서 정의된 바와같은 일반식(V)의 화합물의 제조방법: (a)하기 일반식(Ⅵ) 및 (Ⅶ)의 회합물을 반응시키거나; 또는 (b)하기 일반식(Ⅷ)화합물의 고리화 반응을 실시한다 :상기 식에서, P1, R2, R10, R11, R12및 R13은 제8항에서 정외된 바와같고; P1상의 임의의 치환체는 제8항에서 정의된 바와같고; L은 이탈기이며; R14, R15및 R16은 C1-6알콕시, 아릴옥시, 디-C1-6알킬아디노 및 디아릴아미노로부터 독립적으로 선택되며, R14-R16중의 임의의 두개는페닐렌디옥시를 나타내거나 또는 R14-R16중의 하나는 C1-4알킬, 아릴, 벤질 또는 페닐을 나타내며, 나머지 두개는 C1-4알킬, 트리플루오로메틸 또는 페닐을 나타내며 이때, 임의의 페닐기는 C1-3알킬 또는 C1-3알킬 또는 C1-3알콕시로 치환될 수 있으며; 임의의 작용기는 보호될 수 있다.
- 제8항의 일반식(Ⅳ)의 화합물, 제9항의 일반식(Ⅶ)또는 (Ⅷ)의 화합물 또는 하기 일반식(Ⅸ), (XⅡ) 또는 (XⅣ)의 화합물 :상기 식에서, P1, R2, R10-R13및 R17은 제8항에서 정의된 바와같고, R17은 보호기이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
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GB92400837.8 | 1992-03-26 | ||
EP92400837 | 1992-03-26 | ||
EP92400839 | 1992-03-26 | ||
EP92400837.8 | 1992-03-26 | ||
EP92400839.4 | 1992-03-26 | ||
EP92402700 | 1992-10-02 | ||
EP92402700.6 | 1992-10-02 |
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KR940005626A true KR940005626A (ko) | 1994-03-22 |
KR100287040B1 KR100287040B1 (ko) | 2001-05-02 |
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KR1019930004664A KR100287040B1 (ko) | 1992-03-26 | 1993-03-25 | 항생 화합물 |
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US (1) | US5571805A (ko) |
EP (1) | EP0562855B1 (ko) |
JP (1) | JPH0625244A (ko) |
KR (1) | KR100287040B1 (ko) |
AT (1) | ATE179978T1 (ko) |
CA (1) | CA2091309A1 (ko) |
DE (1) | DE69324846T2 (ko) |
ES (1) | ES2133358T3 (ko) |
Cited By (1)
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US6620575B2 (en) | 1999-02-04 | 2003-09-16 | Applied Materials, Inc | Construction of built-up structures on the surface of patterned masking used for polysilicon etch |
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GB9202298D0 (en) * | 1992-02-04 | 1992-03-18 | Ici Plc | Antibiotic compounds |
ATE207922T1 (de) * | 1994-02-25 | 2001-11-15 | Banyu Pharma Co Ltd | Carbapenem-derivate |
GB9515975D0 (en) | 1995-08-04 | 1995-10-04 | Zeneca Ltd | Chemical compounds |
HRP970281B1 (en) * | 1996-05-28 | 2002-04-30 | Merck & Co Inc | Carbapenem antibiotic, composition and method of preparation |
EP0923545A1 (en) | 1996-08-17 | 1999-06-23 | Zeneca Limited | 3-mercaptopyrrolidines as farnesyl protein transferase inhibitors |
GB9930318D0 (en) | 1999-12-22 | 2000-02-09 | Zeneca Ltd | Novel compounds |
GB9930317D0 (en) | 1999-12-22 | 2000-02-09 | Zeneca Ltd | Novel compounds |
AR035728A1 (es) * | 2001-01-16 | 2004-07-07 | Merck & Co Inc | Proceso perfeccionado para la sintesis de carbapenem |
GB2376313A (en) * | 2001-06-04 | 2002-12-11 | Hewlett Packard Co | Indicating to a user if they are connected to a trusted computer platform |
CN101367815B (zh) * | 2007-06-28 | 2012-07-04 | 山东轩竹医药科技有限公司 | 六元环甲酰胺取代的巯基吡咯烷碳青霉烯化合物 |
CN101362757A (zh) * | 2007-08-09 | 2009-02-11 | 山东轩竹医药科技有限公司 | 磺酰基取代的碳青霉烯类化合物 |
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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 |
EP0182213B1 (en) * | 1984-11-08 | 1990-09-26 | Sumitomo Pharmaceuticals Company, Limited | Carbapenem compounds and production thereof |
GB9107341D0 (en) * | 1991-04-08 | 1991-05-22 | Ici Plc | Antibiotic compounds |
-
1993
- 1993-03-09 CA CA002091309A patent/CA2091309A1/en not_active Abandoned
- 1993-03-25 AT AT93302296T patent/ATE179978T1/de active
- 1993-03-25 EP EP93302296A patent/EP0562855B1/en not_active Expired - Lifetime
- 1993-03-25 DE DE69324846T patent/DE69324846T2/de not_active Expired - Fee Related
- 1993-03-25 KR KR1019930004664A patent/KR100287040B1/ko not_active IP Right Cessation
- 1993-03-25 ES ES93302296T patent/ES2133358T3/es not_active Expired - Lifetime
- 1993-03-26 JP JP5068076A patent/JPH0625244A/ja active Pending
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1994
- 1994-09-08 US US08/302,394 patent/US5571805A/en not_active Expired - Fee Related
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6620575B2 (en) | 1999-02-04 | 2003-09-16 | Applied Materials, Inc | Construction of built-up structures on the surface of patterned masking used for polysilicon etch |
Also Published As
Publication number | Publication date |
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US5571805A (en) | 1996-11-05 |
CA2091309A1 (en) | 1993-09-27 |
ES2133358T3 (es) | 1999-09-16 |
EP0562855B1 (en) | 1999-05-12 |
EP0562855A1 (en) | 1993-09-29 |
KR100287040B1 (ko) | 2001-05-02 |
DE69324846T2 (de) | 1999-09-16 |
ATE179978T1 (de) | 1999-05-15 |
JPH0625244A (ja) | 1994-02-01 |
DE69324846D1 (de) | 1999-06-17 |
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