KR840006008A - 아제티디논 화합물의 제조방법 - Google Patents
아제티디논 화합물의 제조방법 Download PDFInfo
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- KR840006008A KR840006008A KR1019830003938A KR830003938A KR840006008A KR 840006008 A KR840006008 A KR 840006008A KR 1019830003938 A KR1019830003938 A KR 1019830003938A KR 830003938 A KR830003938 A KR 830003938A KR 840006008 A KR840006008 A KR 840006008A
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- Prior art keywords
- group
- nitrobenzyloxycarbonyl
- ethyl
- hydrogen
- pyrrolidin
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- -1 azetidinone compound Chemical class 0.000 title claims 42
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 17
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 17
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 16
- 125000000217 alkyl group Chemical group 0.000 claims 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
- 125000006848 alicyclic heterocyclic group Chemical group 0.000 claims 11
- 238000000034 method Methods 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 9
- 125000000783 acetimidoyl group Chemical group C(C)(=N)* 0.000 claims 8
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000004104 aryloxy group Chemical group 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims 5
- 125000006239 protecting group Chemical group 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 3
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 3
- 125000001984 thiazolidinyl group Chemical group 0.000 claims 3
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical class CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 claims 3
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical class CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims 3
- YCTWGXIFDPOXPX-UHFFFAOYSA-N 1,2,3-trimethylsiline Chemical compound CC1=CC=C[Si](C)=C1C YCTWGXIFDPOXPX-UHFFFAOYSA-N 0.000 claims 2
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims 2
- 125000004986 diarylamino group Chemical group 0.000 claims 2
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 2
- 238000007363 ring formation reaction Methods 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims 2
- 125000006169 tetracyclic group Chemical group 0.000 claims 2
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 claims 1
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 230000000994 depressogenic effect Effects 0.000 claims 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 claims 1
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- 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
- 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
- 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
-
- 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
- C07D477/02—Preparation
- C07D477/04—Preparation by forming the ring or condensed ring systems
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (18)
- 다음 일반식(Ⅱ)의 화합물을 다음 일반식(Ⅲ)의 화합물과 반응시킴을 특징으로 하는 다음 일반식(Ⅰ)화합물의 제조방법.(I) (Ⅱ)(Ⅲ)상기 일반식에서, R1은 수소 또는 히드록시 보호기이며, R2및 R3는 같거나 다르며 각각 수소, 알킬기 또는 아릴기이며, R4는 알킬기, 치환된 알킬기, 지환식 테테로사이클릭기, 아릴기, 방향족 테테로사이클릭기, 알케닐기, 치환된 알케닐기, 알키닐기 또는 치환된 알키닐기이며, R5는 수소 또는 카복시 보호기이며, 또한 R6는 알콕시기, 아릴옥시기, 디알킬아미노기 또는 디알릴아미노기이거나, 또는 두개의 R6는 모두 O-페닐렌 디옥시기이거나 또는 세개의 R6는 모두 구조식 CH2C(-CH2-0-)3의기이며, 여기서 이들은 R6로 나타낸 세개의 기이며 이들은 같거나 다를수 있다.
- 제1항에 있어서, R1은 수소 또는 히드록시보호기이며, R2및 R3는 같거나 다르며 각각 수소, 알킬기 또는 아릴기이며; R4는 알킬기, 치환된 알킬기, 지환식 복소환기, 아릴기 또는 방향족 복소환기이며, R5는 수소 또는 카복시 보호기이며 또한 R6는 알콕시기, 아릴옥시기 또는 디알킬아미노기인 방법.
- 제1항에 있어서, R4가 치환 또는 비치환 지환식 복소환기인 방법.
- 제1항에 있어서, 지환식 복소환기가 아제리디닐, 피롤리디닐, 피페리디닐, 모포리닐, 테트라하이드로피리미디닐, 티아졸리디닐, 옥사조리디닐, 헥사하이드로피리미디닐, 이미다졸리디닐 또는 옥사하이드로아조시닐기인 방법.
- 제1항에 있어서, R1이 트리메틸실린, t-부틸 디메틸실릴, P-니트로벤질, P-니트로벤질옥시카보닐, 알릴옥시카보닐, 2,2,2-트리브로모에톡시카보닐, 1-에톡시에틸 또는 클로로아세틸 기이며; R2및 R3는 모두 수소원자이고 ; R4는 알킬기, 보호 히드록시알킬기, 보호 아미노알킬기, N1,N1,N2-트리메틸아미디 노메틸기, 벤질기, 페닐 또는 2-나프틸기, 1-(P-니트로벤질옥시카보닐) 피톨리딘-3일, 1-아세틸 피롤리딘-3-일, 1-[N-(P-니트로벤질옥시카보닐) 아세트이미도일] 피롤리딘-3-일, 1-(N-메틸아세트이미도일) 피롤리딘-3-일, 1-[N-(P-니트로벤질옥시카보닐) 포름이미도일] 피롤리딘-3-일, 1-(N-메틸포름이미도일) 피롤리딘-3-일, 2-옥소-헥사하이드로피리미딘-5-일, 3,4,5,6-테트라하이드로-2-메틸-피리미딘-5-일 또는 1,4,5,6-테트라하이드로-2-메틸-1(P-니트로벤질옥시카보닐) 피리미딘-5-일기; 1-(1[-(P-니트로벤질옥시카보닐) 피롤리딘-3-일] 에틸, 1-(1-아세틸피롤리딘-3-일)에틸, 1-(1-[N-(P-니트로벤질옥시카보닐)포름이미도일]피롤리딘-3-일)에틸, 1-(1-[N-(P-니트로벤질옥시카보닐)아세트이미도일]피롤리딘-3-일)에틸, 1-(1-아세틸피롤리딘-3-일)에틸, 1-(10[N-(1-(4-[N-(P-니트로벤질옥시카보닐)포름이미도일]피롤리딘-3-일)에틸, 1-(1-[N-(P-니트로벤질옥시카보닐)아세트 이미도일]피롤리딘-3-일)에틸, 1-(4-[N-(P-니트로벤질옥시카보닐)아세트이미도일]모포린-2-일)에틸, 1-[4-(P-니트로벤질옥시카보닐)모포린-2-일)에틸, 1-(4-아세틸모포린-2-일)에틸 또는 2-[(N-P-니트로벤질옥시카보닐포름이미도일)아미노]에틸기 이거나 또는 2-피리딜, 3-피리딜,4-피리딜, 2-티에닐, 3-티에닐, 2-푸릴, 3-푸릴, 1,2,4-트리아졸-3-일 또는 2-티아졸일기이며; R5는 수소위자 또는 메틸, t-부틸, 벤질, 디페닐메틸, P-니트로벤질, O-니트로벤질, 알릴, 2-클로로알릴, 2,2,2-트리클로로에틸, 2,2,2-트리브로모에틸 또는 2-트리메틸실릴에틸기 이면; 또한 R6는 메톡시, 에톡시, 프로폭시, 이소프로폭시, 부톡시, 2급-부톡시, 페녹시, P-톨일옥사, P-에톡시페녹시, 디메틸아미노, 디에틸아미노, 디프로필아미노, 디이소프로필아미노, 디부틸아미노, 디-2급-부틸아미노 또는 디-t-바틸아미노기인 방법.
- 제1항에 있어서, 일반식(Ⅲ)의 화합물이 트리에틸아민산염, 트리프로필 아민산염 또는 트리이소프로필 아민산염인 방법.
- 다음 일반식(Ⅰ)의 화합물을 환화시킴을 특징으로 하는 다음 일반식(Ⅳ)화합물의 제조방법,(I)(Ⅳ)상기 일반식에서, R1은 수소 또는 히드록시 보호기이며, R2및 R3는 같거나 다르며 각각 수소, 알킬기 또는 아닐기 이며, R4는 알킬기, 치환된알킬기, 치환식복소환기, 아릴기 방향족 복소환기, 알케닐기, 치환된 알케닐기, 알키닐기 또는 치환된 알키닐기이며, R5는 수소 또는 카복시 보호기이며, R6는 알콕시기, 아릴옥시기, 디알킬아미노기 또는 디아릴 아미노기 이거나, 또는 두개의 R6는 모두 O-페닐 텐디옥시기 이거나 또는 세개의 R6는 모두 구조식 CH3C(CH2-O-)3의 기이며, 여기서 이들은 R6로 나타낸 세개의 기이며 이들은 같거나 다를수 있다.
- 제7항에 있어서, R1은 수소 또는 히드록시 보호기이며; R2및 R3는 같거나 다르며 각각 수소, 알킬기 또는 아릴기이며; R4는 알킬기, 치횐된알킬기, 지환식복소환기, 아릴기 또는 방향족 복소환기이며; R5는 수소 또는 카복시 보호기이며; 또한 R6는 알콕시기, 아릴옥시기 또는 디알킬아미노기인 방법.
- 제7항에 있어서, R4가 치환 또는 비치환된 지환식 복소환기인 방법.
- 제9항에 있어서, 지환식 복소환기가 아제티디닐, 피롤리디닐, 피페리디닐, 모포티닐, 테트라하이드로피리미디닐, 티아졸리디닐, 옥사조리디닐, 헥사하이드로피리미디닐, 이미다졸리디니 또는 옥타하이드로아조시닐기인 방법.
- 제7항에 있어서, R1이 트리메틸실린, t-부틸디메틸실릴, P-니트로벤질, P-니트로벤질옥시카보닐, 알릴옥시카보닐, 2,2,2-트리브로모에톡시카보닐, 1-에톡시에틸 또는 클로로아세틸 기이며; R2및 R3는 모두 수소원자이고 ; R4는 알킬기, 보호 히드록시알킬기, 보호 아미노알킬기, N1,N1,N2-트리메틸아미디 노메틸기, 벤질기, 페닐 또는 2-나프틸기, 1-(P-니트로벤질옥시카보닐) 피톨리딘-3일, 1-아세틸 피롤리딘-3-일, 1-[N-(P-니트로벤질옥시카보닐) 아세트이미도일] 피롤리딘-3-일, 1-(N-메틸아세트이미도일) 피롤리딘-3-일, 1-[N-(P-니트로벤질옥시카보닐) 포름이미도일] 피롤리딘-3-일, 1-(N-메틸포름이미도일) 피롤리딘-3-일, 2-옥소-헥사하이드로피리미딘-5-일, 3,4,5,6-테트라하이드로-2-메틸-피리미딘-5-일 또는 1,4,5,6-테트라하이드로-2-메틸-1(P-니트로벤질옥시카보닐) 피리미딘-5-일기; 1-(1[-(P-니트로벤질옥시카보닐) 피롤리딘-3-일] 에틸, 1-(1-아세틸피롤리딘-3-일)에틸, 1-(1-[N-(P-니트로벤질옥시카보닐)포름이미도일]피롤리딘-3-일)에틸, 1-(1-[N-(P-니트로벤질옥시카보닐)아세트이미도일]피롤리딘-3-일)에틸, 1-(1-아세틸피롤리딘-3-일)에틸, 1-(10[N-(1-(4-[N-(P-니트로벤질옥시카보닐)포름이미도일]피롤리딘-3-일)에틸, 1-(1-[N-(P-니트로벤질옥시카보닐)아세트 이미도일]피롤리딘-3-일)에틸,1-(4-[N-(P-니트로벤질옥시카보닐) 포름이미도일]모르포린-2-일)에틸, 1-(4-[N-(P-니트로벤질옥시카보닐)아세트이미도일]모포린-2-일)에틸, 1-[4-(P-니트로벤질옥시카보닐)모포린-2-일)에틸, 1-(4-아세틸모포린-2-일)에틸 또는 2-[(N-P-니트로벤질옥시카보닐포름이미도일)아미노]에틸기 이거나 또는 2-피리딜, 3-피리딜,4-피리딜, 2-티에닐, 3-티에닐, 2-푸릴, 3-푸릴, 1,2,4-트리아졸-3-일 또는 2-티아졸일기이며; R5는 수소원자 또는 메틸, t-부틸, 벤질, 디페닐메틸, P-니트로벤질, O-니트로벤질, 알릴, 2-클로로알릴, 2,2,2-트리클로로에틸, 2,2,2-트리브로모에틸 또는 2-트리메틸실릴에틸기 이며; 또한 R6는 메톡시, 에톡시, 프로폭시, 이소프로폭시, 부톡시, 2급-부톡시, 페녹시, P-톨일옥서, P-에톡시페녹시, 디메틸아미노, 디에틸아미노, 디프로필아미노, 디이소프로필아미노, 디부틸아미노, 디-2급-부틸아미노 또는 디-t-부틸아미노기인 방법.
- 제7항에 있어서, 일반식(Ⅲ)의 화합물이 트리에틸아민산염, 트리프로필 아민산염 또는 트리이소프로필아민산염인 방법.
- 다음 일반식(Ⅱ)의 화합물을 다음 일반식(Ⅲ)의 화합물과 반응시키고 수득한 생성물 환화시킴을 특징으로 하는 다음 일반식(Ⅳ)화합물의 제조방법.(Ⅳ) (I)(Ⅲ)상기 일반식에서, R1은 수소 또는 히드록시 보호기이며, R2및 R3는 같거나 다르며 각각 수소, 알킬기 또는 아닐기 이며, R4는 알킬기, 치환된 알킬기, 지환식복소환기, 아릴기 방향족 복소환기, 알케닐기, 치환된 알케닐기, 알키닐기 또는 치환된 알키닐기이며, R5는 수소 또는 카복시 보호기이며, R6는 알콕시기, 아릴옥시기, 디알킬아미노기 또는 디아릴아미노기 이거나, 또는 두개의 R6는 모두 O-페닐디옥시기 이거나 또는 세개의 R6는 모두 구조식 CH3C(CH2-O-)3의 기이며, 여기서 이들은 R6로 나타낸 세개의 기이며 이들은 같거나 다를수 있다.
- 제7항에 있어서, R1은 수소 또는 히드록시 보호기이며; R2및 R3는 같거나 다르며 각각 수소, 알킬기 또는 아릴기이며; R4는 알킬기, 치횐된 알킬기, 지환식복소환기, 아릴기 또는 방향족 복소환기이며; R5는 수소 또는 카복시 보호기이며; 또한 R6는 알콕시기, 아릴옥시기 또는 디알킬아미노기인 방법.
- 제13항에 있어서, R4가 치환 또는 비치환된 지환식 복소환기인 방법.
- 제13항에 있어서, 치환식 복소환기가 아제티디닐, 피롤리디닐, 피페리디닐, 모포티닐, 테트라하이드로피리미디닐, 티아졸리디닐, 옥사조리디닐, 헥사하이드로피리미디닐, 이미다졸리디닐 또는 옥타하이드로아조시닐기인 방법.
- 제12항에 있어서, 일반식(Ⅲ)의 화합물이 트리에틸아민산염, 트리프로필 아민산염 또는 트리이소프로필아민산염인 방법.
- 제12항에 있어서, 일반식(Ⅱ)와 (Ⅲ) 화합물의 반응사이에 생성물의 중간단리 없이 환화하는 방법※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57145574A JPS5946265A (ja) | 1982-08-24 | 1982-08-24 | アゼチジノン誘導体の製造法 |
| JP145574 | 1982-08-24 | ||
| JP158604 | 1982-09-10 | ||
| JP57158604A JPS5951286A (ja) | 1982-09-10 | 1982-09-10 | カルバペネム誘導体の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840006008A true KR840006008A (ko) | 1984-11-21 |
| KR900006449B1 KR900006449B1 (ko) | 1990-08-31 |
Family
ID=26476650
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830003938A KR900006449B1 (ko) | 1982-08-24 | 1983-08-23 | 아제티디논 화합물의 제조방법 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5856556A (ko) |
| EP (1) | EP0102239B1 (ko) |
| KR (1) | KR900006449B1 (ko) |
| CA (1) | CA1232903A (ko) |
| DE (1) | DE3374063D1 (ko) |
| ES (3) | ES525138A0 (ko) |
| FI (1) | FI80887C (ko) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4696923A (en) * | 1984-04-23 | 1987-09-29 | Merck & Co., Inc. | 6-[1-hydroxyethyl]-2-SR8 -1-methyl-1-carbadethiapen-2-em-3-carboxylic acids |
| DK270685A (da) * | 1984-06-29 | 1985-12-30 | Hoffmann La Roche | Carbapenemderivater |
| US4895939A (en) * | 1986-02-24 | 1990-01-23 | Bristol-Myers Company | High percentage β-yield synthesis of carbapenem intermediates |
| ES2053508T3 (es) * | 1986-11-24 | 1994-08-01 | Fujisawa Pharmaceutical Co | Compuestos de acidos 3-pirrolidinil-tio-1-azabiciclo(3.2.0)hept-2-eno-2-carboxilicos. |
| KR880006244A (ko) * | 1986-11-24 | 1988-07-22 | 후지사와 도모 기찌 로 | 3-피롤리디닐티오-1-아자바이스클로[3.2.0]햅트2-엔-2-카르복실산 화합물 및 이의 제조방법 |
| US4820815A (en) * | 1987-09-01 | 1989-04-11 | University Of Notre Dame Du Lac | Azetidinone N-phosphonomethyl esters |
| US4925838A (en) * | 1988-03-18 | 1990-05-15 | Fujisawa Pharmaceutical Company, Ltd. | 3-pyrrolidinylthio-1-azabicyclo[3.2.0]-hept-2-ene-2-carboxylic acid compounds |
| GB8811237D0 (en) * | 1988-05-12 | 1988-06-15 | Fujisawa Pharmaceutical Co | 3-pyrrolidinylthio-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid derivatives |
| US4963544A (en) * | 1988-05-23 | 1990-10-16 | Fujisawa Pharmaceutical Company, Ltd. | 3-pyrrolidinylthio-1-azabicyclo[3.2.0]-hept-2-ene-2-carboxylic acid compounds |
| GB8923844D0 (en) * | 1989-10-23 | 1989-12-13 | Fujisawa Pharmaceutical Co | Carbapenem compounds |
| IL99513A0 (en) * | 1990-09-20 | 1992-08-18 | Hoechst Ag | Process for the preparation of carbapenem compounds |
| GB9103034D0 (en) * | 1991-02-13 | 1991-03-27 | Fujisawa Pharmaceutical Co | Processes for preparing carbapenem derivatives |
| GB9305813D0 (en) * | 1993-03-20 | 1993-05-05 | Glaxo Spa | Chemical process |
| US6395894B2 (en) | 1998-04-16 | 2002-05-28 | Philip J. Pye | Process for the synthesis of carbapenem intermidiates, and compounds produced |
| ATE263766T1 (de) | 1998-06-17 | 2004-04-15 | Merck & Co Inc | Verfahren zur synthese von carbapenem- zwischenprodukten |
| US6194568B1 (en) | 1998-07-13 | 2001-02-27 | Merck & Co., Inc. | Process for synthesizing carbapenem intermediates |
| US7241308B2 (en) * | 2003-06-09 | 2007-07-10 | Xtent, Inc. | Stent deployment systems and methods |
| GB0400382D0 (en) * | 2004-01-09 | 2004-02-11 | Glaxo Group Ltd | Novel processes |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1593524A (en) * | 1976-11-19 | 1981-07-15 | Merck & Co Inc | 1-carba-2-penem-3-carboxylic acids |
| US4348320A (en) * | 1976-11-19 | 1982-09-07 | Merck & Co., Inc. | Substituted azetidiones |
| US4446146A (en) * | 1978-07-26 | 1984-05-01 | Beecham Group Limited | β-Lactam containing compounds, their preparation and use |
| JPS579784A (en) * | 1980-06-23 | 1982-01-19 | Sankyo Co Ltd | Production of penem-3-carboxylic derivative |
| DK329381A (da) * | 1980-07-24 | 1982-01-25 | Takeda Chemical Industries Ltd | Fremgangsmaade til frmstilling af 1,1-disubstitueret carba-z -penem samt salte og estere deraf |
| US4347183A (en) * | 1981-02-02 | 1982-08-31 | Schering Corporation | Process for the synthesis of penems and carbapenems |
| EP0057565A1 (en) * | 1981-02-04 | 1982-08-11 | Beecham Group Plc | Beta-lactam antibiotics, their preparation and use |
| EP0060077A1 (en) * | 1981-03-04 | 1982-09-15 | Beecham Group Plc | Beta-lactam antibiotics, their preparation and use |
-
1983
- 1983-08-23 KR KR1019830003938A patent/KR900006449B1/ko not_active IP Right Cessation
- 1983-08-24 FI FI833034A patent/FI80887C/fi not_active IP Right Cessation
- 1983-08-24 EP EP83304904A patent/EP0102239B1/en not_active Expired
- 1983-08-24 CA CA000435304A patent/CA1232903A/en not_active Expired
- 1983-08-24 ES ES525138A patent/ES525138A0/es active Granted
- 1983-08-24 DE DE8383304904T patent/DE3374063D1/de not_active Expired
-
1984
- 1984-04-12 ES ES531562A patent/ES531562A0/es active Granted
- 1984-04-12 ES ES531561A patent/ES8602796A1/es not_active Expired
-
1993
- 1993-03-23 US US08/035,915 patent/US5856556A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE3374063D1 (en) | 1987-11-19 |
| US5856556A (en) | 1999-01-05 |
| ES8502708A1 (es) | 1985-01-16 |
| ES531561A0 (es) | 1985-12-01 |
| ES8507491A1 (es) | 1985-09-01 |
| FI80887B (fi) | 1990-04-30 |
| ES531562A0 (es) | 1985-09-01 |
| FI833034A0 (fi) | 1983-08-24 |
| CA1232903A (en) | 1988-02-16 |
| ES525138A0 (es) | 1985-01-16 |
| FI833034A (fi) | 1984-02-25 |
| EP0102239A1 (en) | 1984-03-07 |
| FI80887C (fi) | 1990-08-10 |
| EP0102239B1 (en) | 1987-10-14 |
| ES8602796A1 (es) | 1985-12-01 |
| KR900006449B1 (ko) | 1990-08-31 |
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