KR830009087A - 4-플루오로아제티디논의 제조방법 - Google Patents
4-플루오로아제티디논의 제조방법 Download PDFInfo
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- KR830009087A KR830009087A KR1019820000990A KR820000990A KR830009087A KR 830009087 A KR830009087 A KR 830009087A KR 1019820000990 A KR1019820000990 A KR 1019820000990A KR 820000990 A KR820000990 A KR 820000990A KR 830009087 A KR830009087 A KR 830009087A
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- Prior art keywords
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- general formula
- carboxy
- formula
- amino
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- RFGZYLNEARMOGP-UHFFFAOYSA-N 4-fluoroazetidin-2-one Chemical compound FC1CC(=O)N1 RFGZYLNEARMOGP-UHFFFAOYSA-N 0.000 title claims 6
- 238000000034 method Methods 0.000 title claims 4
- -1 hydroxy, carboxy Chemical group 0.000 claims 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000004442 acylamino group Chemical group 0.000 claims 2
- 125000003368 amide group Chemical group 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims 2
- XHFXMNZYIKFCPN-UHFFFAOYSA-N perchloryl fluoride Chemical compound FCl(=O)(=O)=O XHFXMNZYIKFCPN-UHFFFAOYSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims 1
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims 1
- LXKZQNQBTPSVDI-UHFFFAOYSA-N 1-[3-methyl-1-[(4-nitrophenyl)methoxy]-1-oxobut-3-en-2-yl]-4-oxo-3-[(2-phenoxyacetyl)amino]azetidine-2-sulfinic acid Chemical compound C=1C=C([N+]([O-])=O)C=CC=1COC(=O)C(C(=C)C)N(C1=O)C(S(O)=O)C1NC(=O)COC1=CC=CC=C1 LXKZQNQBTPSVDI-UHFFFAOYSA-N 0.000 claims 1
- MGTKVFGCLTZFBN-UHFFFAOYSA-N 2-[2-fluoro-4-oxo-3-[(2-phenoxyacetyl)amino]azetidin-1-yl]-3-methylbut-3-enoic acid Chemical compound O=C1N(C(C(=C)C)C(O)=O)C(F)C1NC(=O)COC1=CC=CC=C1 MGTKVFGCLTZFBN-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- PVEOYINWKBTPIZ-UHFFFAOYSA-M but-3-enoate Chemical compound [O-]C(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-M 0.000 claims 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000004970 halomethyl group Chemical group 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000011591 potassium Chemical group 0.000 claims 1
- 229910052700 potassium Chemical group 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000011734 sodium Chemical group 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 229910052717 sulfur Chemical group 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
Classifications
-
- 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
- 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
- C07D205/09—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 with a sulfur atom directly attached in position 4
- C07D205/095—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 with a sulfur atom directly attached in position 4 and with a nitrogen atom directly attached in position 3
-
- 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
- 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
- C07D205/085—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 with a nitrogen atom directly attached in position 3
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (9)
- 다음 일반식(II)의 아제티디는 화합물을 아프로틱 불활성 유기용매존재하에 -80°내지 -25℃에서 퍼클로릴 플루오라이드와 반응시키고, R이 에스테르화된 카복시로 치환된 3-부테노 에이트일 경우 트리에틸아민 존재하에 메틸렌클로라이드, 디클로로 에탄 또는 클로로포름 같은 불활성 탄화수소 용매내에서 이성화시키고, 4-플루오로아제티디는 이 제조됐을 경우 하이드록시, 카복시 또는 아미노보호그룹 및/또는 아실그룹을 R1으로 부터 제거하여 3-아미노 아제티디논을 제조함을 특징으로하여 다음 일반식(I)의 4-플루오로 아제티디는 및 이의 약학적으로 무독한 염을 제조하는 방법.상기 일반식(I)에서 R1은 아미노 또는(1) 다음 일반식의 이미도그룹,(상기식에서 R2는 C2-C4알킬렌 또는 1,2-페닐렌이다.)(2) 다음 일반식의 아미도그룹,(상기식에서 R3는 a) 수소, C1-C4알킬, 할로메틸, 시아노메틸, 벤질옥시, p-니트로벤질옥시, 3급-부틸옥시, 2,2,2-트리클로로에톡시 또는 p-메톡시벤질옥시;b) 그룹 R'(여기서R'는 페닐; 또는 하나 또는 두개의 할로겐, 하이드록시, 사호된 하이드록시, 니트로, 시아노, C1-C4알킬 또는 C1-C4알콕시로 치환된 페닐임);c) 다음 일반식의 그룹; 또는R＂-(Q)m-CH2-(상기식에서 R＂;는 상술한 R', 1,4-사이클로헥사디에닐, 티에닐 또는 푸릴이고, m은 0 또는 1이고 Q는 산소 또는 황이고, 단, m이 1일 경우 R＂는 R'이다.)d) 다음 일반식의 그룹이다.(상기식에서 R＂는 전술한 바와 같고, W는 하이드록시, 보호된 하이드록시, 카복시, 보호된 카복시, 아미노 또는 보호된 아미노이다.)3) 다음 일반식의 이미다졸리디닐 그룹, 또는(상기식에서 R＂는 전술한 바와 같고, u는 니트로소 또는 아세틸이다.)4) 다음 일반식의 이미도 그룹이고(상기식에서 R'는 전술한 바와 같고 n은 0 또는 1이고 R4는 C1-C4알킬, C1-C4할로알킬, C1-C4알콕시 또는 2,2,2,-트리클로로에톡시이다.)R은 다음 일반식의 카복시-치환 또는 에스테르화된 카복시-치환부테닐 그룹이고,(상기식에서 R5는 수소 또는 카복시 보호그룹이다.)상기 일반식(II)에서 R은 전술한 바와 같은, 에스테르화된 카복시로 치환된 부테닐그룹이고, R5는 카복시보호그룹이고, R1은 진술한 바와 같은, 아실아미노 또는 이미도그룹이고, W는 보호된 하이드록시, 카복시 또는 아미도그룹이고, M은 수소, 나트륨 또는 칼륨이다.
- 제1항에 있어서, R이 다음 구조식의 그룹인 일반식(I)의 4-플루오로아제티디논을 제조하는 방법.
- 제1항에 있어서, R이 다음 구조식의 그룹인 일반식(I)의 4-플루오로아제티디논을 제조하는 방법.
- 제1 내지 3항중 하나에 있어서, R1이 다음 일반식의 아실아미노 그룹인 일반식(I)의 4-플루오로아제티디논을 제조하는 방법.
- 제1 내지 4항중 하나에 있어서, R3가 일반식 R＂-(Q)m-CH2의 그룹인 일반식(I)의 4-플루오로아제티디논을 제조하는 방법.
- 제1항에 있어서, R1이 아미노, 벤질옥시카보닐아미노, p-니트로벤질옥시카보닐아미노, 3급-부틸옥시카보닐아미노, 2,2,2-트리클로로에톡시카보닐아미노 또는 p-에톡시벤질옥시카보닐아미노를 제외하고는 상술한 R1과 같고 R이 다음 일반식의 카복시-치환 부테닐 그룹인 일반식(I)의 4-플루오로 아제티논을 제조하는 방법.(여기서 R5는 수소이다).
- 제1 내지 43항 및 5항중 하나에 있어서, R1이 아미노인 일반식(I)의 4-플루오로아제티디논을 제조하는 방법.
- 제1항에 있어서, p-니트로벤질 3-메틸-2-(2-옥소-4-설피노-3-페녹시아세트아미도-1-아제티디닐)-3-부테노 에이트가 함유된 메틸렌 클로라이드 용액을 디메틸포름아미드존재하에 -78℃에서 퍼클로릴 플루오라이드와 약 25분간 반응시켜 p-니트로벤진 3-메틸-2-(2-옥소-4-플루오로-3-페녹시아세트아미도-1-아제티디닐)-3-부테노에이트를 제조하는 방법.
- 제1항에 있어서, 제8항의 방법에 의해 제조된 p-니트로벤질 3-메틸-2-(2-옥소-4-플루오로-3-페녹시아세트아미도-1-아제티디닐)-3-부테노에이트를 메틸렌클로라이드내에서 트리에틸아민 존재하에 실온에서 30분간 교반하며 이성화시켜 p-니트로벤질 3-메틸-2-(2-옥소-4-플루오로-3-페녹시아세트아미도-1-아제티디닐)-2-부테노에이트를 제조하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24198981A | 1981-03-09 | 1981-03-09 | |
| US241,989 | 1981-03-09 | ||
| US241.989 | 1981-03-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830009087A true KR830009087A (ko) | 1983-12-17 |
| KR850001879B1 KR850001879B1 (ko) | 1985-12-28 |
Family
ID=22913020
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8200990A KR850001879B1 (ko) | 1981-03-09 | 1982-03-08 | 4-플루오로 아제티디논의 제조방법 |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0060119B1 (ko) |
| JP (1) | JPS57159760A (ko) |
| KR (1) | KR850001879B1 (ko) |
| CA (1) | CA1173837A (ko) |
| DE (1) | DE3262931D1 (ko) |
| DK (1) | DK99582A (ko) |
| GB (1) | GB2094306B (ko) |
| GR (1) | GR74762B (ko) |
| HU (1) | HU188781B (ko) |
| IE (1) | IE52580B1 (ko) |
| IL (1) | IL65158A0 (ko) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0117053A1 (en) * | 1983-02-10 | 1984-08-29 | Ajinomoto Co., Inc. | Azetidinone derivatives |
| US5631365A (en) | 1993-09-21 | 1997-05-20 | Schering Corporation | Hydroxy-substituted azetidinone compounds useful as hypocholesterolemic agents |
-
1982
- 1982-03-03 IL IL65158A patent/IL65158A0/xx unknown
- 1982-03-04 CA CA000397601A patent/CA1173837A/en not_active Expired
- 1982-03-05 GR GR67510A patent/GR74762B/el unknown
- 1982-03-05 HU HU82692A patent/HU188781B/hu unknown
- 1982-03-08 KR KR8200990A patent/KR850001879B1/ko active
- 1982-03-08 DE DE8282301165T patent/DE3262931D1/de not_active Expired
- 1982-03-08 EP EP82301165A patent/EP0060119B1/en not_active Expired
- 1982-03-08 IE IE516/82A patent/IE52580B1/en unknown
- 1982-03-08 GB GB8206710A patent/GB2094306B/en not_active Expired
- 1982-03-08 DK DK99582A patent/DK99582A/da not_active Application Discontinuation
- 1982-03-09 JP JP57037900A patent/JPS57159760A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IE52580B1 (en) | 1987-12-23 |
| JPS57159760A (en) | 1982-10-01 |
| HU188781B (en) | 1986-05-28 |
| EP0060119B1 (en) | 1985-04-10 |
| GR74762B (ko) | 1984-07-12 |
| KR850001879B1 (ko) | 1985-12-28 |
| DE3262931D1 (en) | 1985-05-15 |
| GB2094306A (en) | 1982-09-15 |
| EP0060119A1 (en) | 1982-09-15 |
| CA1173837A (en) | 1984-09-04 |
| IL65158A0 (en) | 1982-05-31 |
| IE820516L (en) | 1982-09-09 |
| DK99582A (da) | 1982-09-10 |
| GB2094306B (en) | 1985-03-13 |
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