KR850002988A - 페니실린 유도체의 제조방법 - Google Patents
페니실린 유도체의 제조방법 Download PDFInfo
- Publication number
- KR850002988A KR850002988A KR1019840006357A KR840006357A KR850002988A KR 850002988 A KR850002988 A KR 850002988A KR 1019840006357 A KR1019840006357 A KR 1019840006357A KR 840006357 A KR840006357 A KR 840006357A KR 850002988 A KR850002988 A KR 850002988A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- compound
- alkyl
- hydrogen
- penicillin
- Prior art date
Links
- 150000002960 penicillins Chemical class 0.000 title claims 4
- 150000001875 compounds Chemical class 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 229930182555 Penicillin Natural products 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 5
- -1 cyano, formyl Chemical group 0.000 claims 5
- 238000005886 esterification reaction Methods 0.000 claims 5
- 229940049954 penicillin Drugs 0.000 claims 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 230000032050 esterification Effects 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 238000005755 formation reaction Methods 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000004756 (C2-C7) alkoxycarbonylamino group Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims 2
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000005225 alkynyloxycarbonyl group Chemical group 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
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 238000007257 deesterification reaction 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
- 125000006239 protecting group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims 1
- 125000006515 benzyloxy alkyl group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 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 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/86—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with only atoms other than nitrogen atoms directly attached in position 6 and 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula, e.g. penicillins, penems
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (3)
- 하기 일반식(Ⅱ)의 화합물을 하기 일반식(Ⅲ)의 화합물과 반응시키고, N5또는 N6가 C8~13벤질옥시 알킬일 때, 생성된 하기 일반식(Ⅳ)의 화합물을 탈벤질화반응시킨 다음, 필요하다면 탈에스테르화, 탈에스테르화에 이은 에스테르화, 에스테르 상호 교환반응 또는 염형성 반응 시킴을 특징으로하는 하기 일반식(Ⅰ-1)의 페니실린 유도체의 제조방법.상기 식중, R7, 및 R8는 같거나 서로 다르며, 수소, C1~6알킬, C1~6히드록시알킬, C3~9아실옥시알킬 C8~13벤질옥시알킬, C2~7알콕시알킬, C2~7알콕시카르보닐, C3~8알케닐옥시카르보닐, C3~8알키닐옥시카르보닐, 페닐, 시아노, 포르밀, 트리플루오로메틸, C2~6아실, 카르바모일 또는 C2~7알킬카르바모일을 나타내고; R3는 수소, 약학적으로 수용할 수 있는 염을 형성 하는기 또는 페니실린 카르복실 보호기이며; R7′및 R8′는 동시에 수소 또는 C2~7알콕시카르보닐이 아니고, R7′및 R8′중 하나가 수소일 때 다른 하나는 C2~7알콕시카르보닐이 아니며; R4는 페니실릴 카르복실 보호기이고; R5및 R6는 같거나 서로 다르며, 수소, C1~6알킬, C3~9아실옥시알킬, C2~13벤질옥시알킬, C2~7알콕시알킬, C2~7알콕시카르보닐, C3~8알케닐옥시카르보닐, C3~8알키닐옥시카르보닐, 페닐, 시아노, 포르밀, 트리플루오로메틸, C2~6아실, 카르바모일 또는 C2~7알킬카르바모일을 나타낸다.
- 하기 일반식(Ⅱ)의 화합물을 하기 일반식(Ⅴ)의 비닐 화합물과 반응시켜 하기 일반식(Ⅵ)의 화합물을 수득하고, 필요하다면 탈에스테르화, 탈에스테르화에 이은 에스테르화, 에스테르 상호 교환반응 또는 염형성 반응 시킴을 특징으로하는 하기 일반식(Ⅰ-2)의 페니실린 유도체의 제조방법.상기 식중, R10은 C1~6알킬이고, R3는 수소, 약학적으로 수용할 수 있는 염을 형성 하는기 또는 페니실린 카르복실 보호기이며, R4는 페니실린 카르복실 보호기이고, R9은 C2~5아실옥시 또는 벤조일옥시이며, R10은 C1~6알킬이다.
- 하기 일반식(Ⅶ)의 화합물을 하기 일반식(Ⅷ)의 알콜과 반응시켜 하기 일반식(Ⅰ-d)의 화합물을 수득하고, 필요하다면 일반식(Ⅰ-d)의 화합물을 촉매환원시켜하기 일반식(Ⅰ-e)의 화합물을 수득하고, 필요하다면 일반식(Ⅰ-d) 또는 (Ⅰ-e)의 화합물을 탈에스테르화, 탈에스테르화에 이은 에스테르화, 에스테르 상호 교환 반응 또는 염형성 반응 시킴을 특징으로 하는 하기 일반식(Ⅰ-3)의 페니실린 유도체의 제조방법.상기 식중, R13는 아미노, 벤질옥시카르보닐아미노 또는 C2~7알콕시카르보닐아미노이고, R3는 수소, 약학적으로 수용할 수 있는 염을 형성하는 기 또는 페니실린카르보실 보호기이며, R4는 페니실린 카르복실 보호기이고, R11은 벤질 또는 C1~6알킬이며, R12는 C2~7알콕시카르보닐아미노 또는 벤질옥시카르보닐아미노이고, R, 는 수소, 또는 벤질, P-니트로벤질 및 디페닐메틸을 제외한 페니실린 카르복실 보호기이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP192040/83 | 1983-10-13 | ||
| JP58192040A JPS6084291A (ja) | 1983-10-13 | 1983-10-13 | ペニシリン誘導体 |
| JP192040 | 1983-10-13 | ||
| JP71499/84 | 1984-04-09 | ||
| JP71499 | 1984-04-09 | ||
| JP59071499A JPS60215688A (ja) | 1984-04-09 | 1984-04-09 | ペニシリン誘導体 |
| JP78064/84 | 1984-04-18 | ||
| JP59078064A JPS60222488A (ja) | 1984-04-18 | 1984-04-18 | ペニシリン誘導体 |
| JP78064 | 1984-04-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR850002988A true KR850002988A (ko) | 1985-05-28 |
| KR900007183B1 KR900007183B1 (ko) | 1990-09-29 |
Family
ID=27300661
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840006357A Expired KR900007183B1 (ko) | 1983-10-13 | 1984-10-13 | 페니실린 유도체의 제조방법 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4668514A (ko) |
| EP (1) | EP0138523B1 (ko) |
| KR (1) | KR900007183B1 (ko) |
| AU (1) | AU550560B2 (ko) |
| CA (1) | CA1239392A (ko) |
| DE (1) | DE3465475D1 (ko) |
| ES (2) | ES8604601A1 (ko) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8624628D0 (en) * | 1986-10-14 | 1986-11-19 | Scras | Soluble/splitable tablets |
| US4891369A (en) * | 1986-12-03 | 1990-01-02 | Taiho Pharmaceutical Company, Limited | 2β-Substituted-methylpenicillanic acid derivatives, and salts and esters thereof |
| JP2602685B2 (ja) * | 1988-03-01 | 1997-04-23 | 大鵬薬品工業株式会社 | ２α−メチル−２β―（１，２，３−トリアゾール−１−イル）メチルペナム−３α−カルボン酸誘導体の製造法 |
| JP2599610B2 (ja) * | 1988-03-01 | 1997-04-09 | 大鵬薬品工業株式会社 | ２β―置換メチルペニシリン誘導体の製造法 |
| US4958020A (en) * | 1989-05-12 | 1990-09-18 | American Cyanamid Company | Process for producing β-lactamase inhibitor |
| KR100671881B1 (ko) * | 2002-06-07 | 2007-01-19 | 오키드 케미칼즈 앤드 파마수티컬즈 리미티드 | 세팜 유도체로부터의 페남 유도체 제조방법 |
| US20060173177A1 (en) * | 2005-01-28 | 2006-08-03 | Gego Csaba L | Process for preparation of penam derivatives |
| JP4579021B2 (ja) * | 2005-03-23 | 2010-11-10 | ヒロセ電機株式会社 | 電気コネクタ |
| US11040987B2 (en) * | 2019-09-11 | 2021-06-22 | Tennor Therapeutics Limited | Penam derivatives for treating bacterial infections |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58185589A (ja) * | 1982-04-23 | 1983-10-29 | Taiho Yakuhin Kogyo Kk | ペニシリン誘導体 |
| AU541028B2 (en) * | 1982-06-21 | 1984-12-13 | Taiho Pharmaceutical Co., Ltd. | 6-unsubstituted penicillin derivatives |
| US4562073A (en) * | 1982-12-24 | 1985-12-31 | Taiho Pharmaceutical Company Limited | Penicillin derivatives |
-
1984
- 1984-10-02 CA CA000464517A patent/CA1239392A/en not_active Expired
- 1984-10-03 AU AU33787/84A patent/AU550560B2/en not_active Ceased
- 1984-10-05 US US06/658,373 patent/US4668514A/en not_active Expired - Fee Related
- 1984-10-05 DE DE8484306788T patent/DE3465475D1/de not_active Expired
- 1984-10-05 EP EP84306788A patent/EP0138523B1/en not_active Expired
- 1984-10-11 ES ES536964A patent/ES8604601A1/es not_active Expired
- 1984-10-13 KR KR1019840006357A patent/KR900007183B1/ko not_active Expired
-
1985
- 1985-10-01 ES ES548129A patent/ES8605276A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES8605276A1 (es) | 1986-04-01 |
| EP0138523A1 (en) | 1985-04-24 |
| ES8604601A1 (es) | 1986-02-16 |
| ES548129A0 (es) | 1986-04-01 |
| US4668514A (en) | 1987-05-26 |
| KR900007183B1 (ko) | 1990-09-29 |
| CA1239392A (en) | 1988-07-19 |
| AU550560B2 (en) | 1986-03-27 |
| EP0138523B1 (en) | 1987-08-19 |
| ES536964A0 (es) | 1986-02-16 |
| AU3378784A (en) | 1985-04-18 |
| DE3465475D1 (en) | 1987-09-24 |
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Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19841013 |
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Patent event code: PA02012R01D Patent event date: 19880805 Comment text: Request for Examination of Application Patent event code: PA02011R01I Patent event date: 19841013 Comment text: Patent Application |
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Comment text: Decision on Publication of Application Patent event code: PG16051S01I Patent event date: 19900831 |
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