KR860007201A - 항생 작용을 갖는 악타가르딘의 염기성 모노카르복시아미드 유도체의 제조방법 - Google Patents
항생 작용을 갖는 악타가르딘의 염기성 모노카르복시아미드 유도체의 제조방법 Download PDFInfo
- Publication number
- KR860007201A KR860007201A KR1019860002100A KR860002100A KR860007201A KR 860007201 A KR860007201 A KR 860007201A KR 1019860002100 A KR1019860002100 A KR 1019860002100A KR 860002100 A KR860002100 A KR 860002100A KR 860007201 A KR860007201 A KR 860007201A
- Authority
- KR
- South Korea
- Prior art keywords
- hydrogen
- group
- alkyl
- acttagardine
- alkyl group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 15
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 title 1
- 230000003115 biocidal effect Effects 0.000 title 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 150000001412 amines Chemical class 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims 1
- NADTUDXSPFPHPK-UHFFFAOYSA-N B.[Na] Chemical compound B.[Na] NADTUDXSPFPHPK-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- ZDRJMZMVJTUQHH-UHFFFAOYSA-N borane;potassium Chemical compound B.[K] ZDRJMZMVJTUQHH-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 150000001728 carbonyl compounds Chemical class 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 claims 1
- LAWKVNVCUPIOMG-HWWYPGLISA-N gardimycin Chemical compound C1=CC=C2C(C[C@H](C(=O)NCC(=O)N[C@H](CO)C(=O)N[C@H](C)C(=O)NCC(=O)N[C@H](CC)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](C)C(=O)N[C@@H](C)C(=O)N[C@H](C)C(O)=O)C(C)C)NC(=O)[C@@H](NC(=O)[C@@H](C)NC(=O)[C@@H](CC)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@@H](CC)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)N)[C@@H](C)CC)C(C)C)=CNC2=C1 LAWKVNVCUPIOMG-HWWYPGLISA-N 0.000 claims 1
- 108010070411 gardimycin Proteins 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000006722 reduction reaction Methods 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P1/00—Preparation of compounds or compositions, not provided for in groups C12P3/00 - C12P39/00, by using microorganisms or enzymes
- C12P1/06—Preparation of compounds or compositions, not provided for in groups C12P3/00 - C12P39/00, by using microorganisms or enzymes by using actinomycetales
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/06—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
-
- 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
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/20—Bacteria; Culture media therefor
- C12N1/205—Bacterial isolates
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/045—Actinoplanes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Mycology (AREA)
- Virology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Compounds Of Unknown Constitution (AREA)
- Cephalosporin Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (15)
- 하기 일반식(I)으로 표시되는 앙타가르딘의 염기성 모노아미드 유도체 및 그의 산 염기 부가 염의 제조방법에 있어서,상기 식중,기는 악타가르딘 핵이고, R는기로서, 여기에서 R1및 R2는 독립적으로 수소 또는 일반식(식중, n는 2 내지 8의 정수이고, R3및 R4는 독립적으로 수소 또는 (C1-C4)알킬기이거나, 또는 R3와 R4가 함께 -(CH2)3-, -(CH2)4-, -(CH2)2-0---(CH2)2-, -(CH2)2-S-(CH2)2- 또는 -(CH2)5-기를 나타냄)의 기이거나, 또는 R1과 R2가 이에 결합된 질소원자와 함께 피페라진 부분[이 피페라진 부분은 4위치에서 (C1-C4)알킬, (C5-C7)시클로알킬, 벤질 및 치환벤질기(여기에서, 페닐 부분은 클로로, 브로모, 니트로, (C1-C4)알킬 및 (C1-C4)알콕시기 중에서 선택되는 1 또는 2개의 치환체를 함유함) 중에서 선택되는 치환체로 치환될 수 있음]을 나타내나, 단 R1과 R2는 동시에 수소일 수 없고, R6는 수소, (C1-C4)알킬 또는 (C1-C4)알콕시 (C2-C4)알킬기이고, R6는 수소 또는 (C1-C4)알킬기임}, 악타가르딘을 0℃ 내지 실온 사이의 온도에서, 악타가르딘 보다 약간 과량의 적합한 축합제 존재하에 유기 용매 중에서 일반식 RH(여기에서, R는 상기 정의한 바와 같음)의 아민 몰 과량과 반응시키되, a) R5가 (C1-C4)알킬 또는 (C1-C4)알콕시 (C2-C4)알킬기인 화합물이 요구되는 경우에는, R5가 수소인 대응하는 화합물을 산매질중에서 일반식 R5OH(여기에서, R5는 (C1-C4)알킬 또는 (C1-C4)알콕시 (C2-C4)알킬기임)의 알코올과 반응시켜서 에스테르화시키고, b) R6가 (C1-C4)알킬기인 화합물이 요구되는 경우에는, R6가 수소인 대응하는 화합물을 적합한 카르보닐 화합물과 반응시켜서 중간생성물을 생성시키고, 이어서 이것을 적합한 환원제를 사용해서 환원시켜서 환원성 알킬화 시킴을 특징으로 하는 방법.
- 제1항에 있어서, R가 다음과 같은 기로 되는 군 중에서 선택되는 기인 방법.
- 제1항에 있어서, R가 다음과 같은 기로 되는 군 중에서 선택되는 기인 방법.
- 제1항에 있어서, R가 NHCH2CH2CH2N(CH3)2기인 화합물 또는 이에 대응하는 약물학적으로 허용되는 산부가염의 제조 방법.
- 제1항에 있어서, R5및 R6가 수소인 방법.
- 제1항에 있어서, R5가 수소이고, R6가 (C1-C4)알킬기인 방법.
- 제1항에 있어서, b) 에서의 환원반응을 수소화 보론 나트륨 또는 수소화 보론 칼륨 존재하에 행하는 방법.
- 제1항에 있어서, 아민 RH를 악타가르딘 보다 2 내지 6배 몰 과량으로 존재시키는 방법.
- 제1항에 있어서, 아민 RH를 악타가르딘 보다 3 내지 5배 몰 과량으로 존재시키는 방법.
- 제1항에 있어서, 아민 RH를 악타가르딘 보다 4배 몰 과량으로 존재시키는 방법.
- 제1항에 있어서, 불활성 유기 용매가 디메틸포름아미드인 방법.
- 제1항에 있어서, 온도가 0°내지 30℃ 사이인 방법.
- 제1항에 있어서, 온도가 0°내지 5℃ 사이인 방법.
- 제1항에 있어서, 적합한 축합제가 디페닐포스표릴아지드인 방법.
- 제1항에 있어서, 디페닐포스포릴아지드를 악타가르딘 몰 당 1.1 내지 3몰로 존재시키는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8507528 | 1985-03-22 | ||
GB858507528A GB8507528D0 (en) | 1985-03-22 | 1985-03-22 | Basis monocarboxyamide derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
KR860007201A true KR860007201A (ko) | 1986-10-08 |
Family
ID=10576477
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019860002100A KR860007201A (ko) | 1985-03-22 | 1986-03-21 | 항생 작용을 갖는 악타가르딘의 염기성 모노카르복시아미드 유도체의 제조방법 |
Country Status (13)
Country | Link |
---|---|
US (1) | US4684644A (ko) |
EP (1) | EP0195359B1 (ko) |
JP (1) | JPS61227529A (ko) |
KR (1) | KR860007201A (ko) |
AT (1) | ATE48608T1 (ko) |
CA (1) | CA1259985A (ko) |
DE (1) | DE3667469D1 (ko) |
DK (1) | DK165120C (ko) |
ES (1) | ES8705893A1 (ko) |
GB (1) | GB8507528D0 (ko) |
HU (1) | HU199510B (ko) |
IL (1) | IL78181A0 (ko) |
ZA (1) | ZA861424B (ko) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8711066D0 (en) * | 1987-05-11 | 1987-06-17 | Lepetit Spa | Teicoplanin derivatives |
DE19745583A1 (de) * | 1997-10-15 | 1999-04-22 | Hoechst Marion Roussel De Gmbh | Neues Lantibiotikum verwandt mit Actagardine, Verfahren zur Herstellung und Verwendung derselben |
GB0600928D0 (en) | 2006-01-17 | 2006-02-22 | Novacta Biosystems Ltd | Improvements relating to lantibiotics |
GB0714030D0 (en) | 2007-07-18 | 2007-08-29 | Novacta Biosystems Ltd | The use of type-B lantibiotic-based compounds having antimicrobial activity |
GB0714029D0 (en) | 2007-07-18 | 2007-08-29 | Novacta Biosystems Ltd | Lantibiotic-based compounds having antimicrobial activity |
GB0900599D0 (en) | 2009-01-14 | 2009-02-18 | Novacta Biosystems Ltd | Treatment |
JP5719312B2 (ja) * | 2009-01-14 | 2015-05-13 | ノヴァクタ バイオシステムズ リミティッド | デオキシアクタガルジン誘導体 |
TWI504610B (zh) * | 2009-02-04 | 2015-10-21 | Novacta Biosystems Ltd | 阿肽加定衍生物、其製備方法及其用途 |
GB201001688D0 (en) | 2010-02-02 | 2010-03-17 | Novacta Biosystems Ltd | Compounds |
JP5852966B2 (ja) | 2010-02-02 | 2016-02-03 | ノヴァクタ バイオシステムズ リミティッド | ランチビオティックの塩 |
GB201013507D0 (en) | 2010-08-11 | 2010-09-22 | Novacta Biosystems Ltd | Compounds |
GB201013509D0 (en) | 2010-08-11 | 2010-09-22 | Novacta Biosystems Ltd | Compounds |
GB201013508D0 (en) | 2010-08-11 | 2010-09-22 | Novacta Biosystems Ltd | Compounds |
GB201013513D0 (en) | 2010-08-11 | 2010-09-22 | Novacta Biosystems Ltd | Formulations |
CN102993188A (zh) * | 2012-11-03 | 2013-03-27 | 浙江大学 | 弗霉素b及其制备方法和用途 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1470407A (en) * | 1974-07-27 | 1977-04-14 | Lepetit Spa | Antibiotic substances |
-
1985
- 1985-03-22 GB GB858507528A patent/GB8507528D0/en active Pending
-
1986
- 1986-02-26 ZA ZA861424A patent/ZA861424B/xx unknown
- 1986-03-12 EP EP86103296A patent/EP0195359B1/en not_active Expired
- 1986-03-12 AT AT86103296T patent/ATE48608T1/de not_active IP Right Cessation
- 1986-03-12 DE DE8686103296T patent/DE3667469D1/de not_active Expired - Fee Related
- 1986-03-18 DK DK123386A patent/DK165120C/da not_active IP Right Cessation
- 1986-03-18 IL IL78181A patent/IL78181A0/xx not_active IP Right Cessation
- 1986-03-21 CA CA000504714A patent/CA1259985A/en not_active Expired
- 1986-03-21 KR KR1019860002100A patent/KR860007201A/ko not_active Application Discontinuation
- 1986-03-21 US US06/842,523 patent/US4684644A/en not_active Expired - Fee Related
- 1986-03-21 HU HU861200A patent/HU199510B/hu not_active IP Right Cessation
- 1986-03-21 ES ES553227A patent/ES8705893A1/es not_active Expired
- 1986-03-22 JP JP61064671A patent/JPS61227529A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
GB8507528D0 (en) | 1985-05-01 |
ES8705893A1 (es) | 1987-05-16 |
HUT40455A (en) | 1986-12-28 |
HU199510B (en) | 1990-02-28 |
JPS61227529A (ja) | 1986-10-09 |
ZA861424B (en) | 1986-12-30 |
ATE48608T1 (de) | 1989-12-15 |
DK123386A (da) | 1986-09-23 |
EP0195359A3 (en) | 1987-12-09 |
DK165120C (da) | 1993-03-01 |
DE3667469D1 (de) | 1990-01-18 |
IL78181A0 (en) | 1986-07-31 |
EP0195359A2 (en) | 1986-09-24 |
US4684644A (en) | 1987-08-04 |
DK165120B (da) | 1992-10-12 |
DK123386D0 (da) | 1986-03-18 |
ES553227A0 (es) | 1987-05-16 |
CA1259985A (en) | 1989-09-26 |
EP0195359B1 (en) | 1989-12-13 |
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