KR850002989A - 카르복시알켄아미도 세팔로스포린의 제조방법 - Google Patents
카르복시알켄아미도 세팔로스포린의 제조방법 Download PDFInfo
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- KR850002989A KR850002989A KR1019840006134A KR840006134A KR850002989A KR 850002989 A KR850002989 A KR 850002989A KR 1019840006134 A KR1019840006134 A KR 1019840006134A KR 840006134 A KR840006134 A KR 840006134A KR 850002989 A KR850002989 A KR 850002989A
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- Prior art keywords
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- hydrogen
- atom
- thiaalkylene
- halogen
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- 229930186147 Cephalosporin Natural products 0.000 title claims 5
- 229940124587 cephalosporin Drugs 0.000 title claims 5
- 150000001780 cephalosporins Chemical class 0.000 title claims 5
- 238000000034 method Methods 0.000 title claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 239000001257 hydrogen Substances 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 15
- 125000004429 atom Chemical group 0.000 claims 14
- 150000002148 esters Chemical class 0.000 claims 14
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 150000002367 halogens Chemical class 0.000 claims 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 14
- 125000003118 aryl group Chemical group 0.000 claims 9
- 125000002947 alkylene group Chemical group 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 238000004519 manufacturing process Methods 0.000 claims 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 239000011593 sulfur Chemical group 0.000 claims 4
- 229910021653 sulphate ion Chemical group 0.000 claims 4
- 239000012442 inert solvent Substances 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 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 2
- 230000001681 protective effect Effects 0.000 claims 2
- UTRQNVVDCDOSNA-UHFFFAOYSA-N 2-formyloxy-2-oxoacetic acid Chemical compound OC(=O)C(=O)OC=O UTRQNVVDCDOSNA-UHFFFAOYSA-N 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 1
- 235000009392 Vitis Nutrition 0.000 claims 1
- 241000219095 Vitis Species 0.000 claims 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- -1 alkylidene phosphoran Chemical compound 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 238000006664 bond formation reaction Methods 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 claims 1
- 238000006114 decarboxylation reaction Methods 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 239000012434 nucleophilic reagent Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000002516 radical scavenger Substances 0.000 claims 1
- 150000003462 sulfoxides Chemical class 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
- C07D261/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D503/00—Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxapenicillins, clavulanic acid derivatives; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- 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
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65613—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system (X = CH2, O, S, NH) optionally with an additional double bond and/or substituents, e.g. cephalosporins and analogs
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Photoreceptors In Electrophotography (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (7)
- 하기일반식(Ⅱ)로 표시되는 7베타-아미노-3-세펨-4-카르복시산 유도체 또는 그의 반응성유도체를 하기 일반식(Ⅲ)으로 표시되는 카르복시알켄산 또는 그의 반응성 유도체로 아미드와 시킴을 특징으로 하는 하기 일반식(Ⅰ)로 표시되는 7베타-(카르복시알케노일아미노)-3-세펨-4-카르복시산화합물 및 그의 유도체의 제조방법.(상기 식중, R은 아릴 또는 복소환기이고; R1은 수소 또는 할로겐이고; R2는 단일결합, 알킬렌, 또는 티아알킬렌이고; R3는 수소원자, 염형성원자 또는 기, 또는 에스테르 형성기이고; R4는 수소 또는 메톡시이고; R5는 수소 또는 세팔로스포린의 3-치환기이고, R6는 수소원자, 염형성 원자 또는 기, 또는 에스테르 형성기이고; X는 산소, 황, 또는 술피닐이며, 단 R이 티아알킬렌일때 R1은 할로겐이다.)
- 하기 일반식(Ⅰ)로 표시되는 7베타-(카르복시알케노일아미노)-3-세펨-4-카르복시산 또는 그의 반응성 유도체를 염기로 중화시킴을 특징으로 하는 하기 일반식(Ⅰ)로 표시되는 염 및 그의 유도체의 제조방법.(상기 식중, R은 아릴 또는 복소환기이고; R1은 수소 또는 할로겐이고; R2는 단일결합, 알킬렌, 또는 티아알킬렌이고; R3는 수소원자, 염형성원자 또는 기, 또는 에스테르 형성기이고; R4는 수소 또는 메톡시이고; R5는 수소 또는 세팔로스포린의 3-치환기이고, R6는 수소원자, 염형성 원자 또는 기, 또는 에스테르 형성기이고; X는 산소, 황, 또는 술피닐이며, 단 R이 티아알킬렌일때 R1은 할로겐이고, R3및 R6중 최소한 하나는 수소이다.)
- 대응 3-(하드록시, 아실옥시 또는 할로) 세팜의 염기 또는 열제거 반응에 의한 3-이중결합형성, 술폭시드환원, 3-(할로 또는 3-술포닐옥시) 세펨의 환원 및 3-(이탈기치환) 메틸-3-세펨을 대응 친핵성 시약으로 대치시키는 방법중에서 선택된 공지의 방법으로 3-작용기를 도입함을 특징으로하는 하기 일반식(Ⅰ)로 표시되는 화합물의 제조방법.(상기 식중, R은 아릴 또는 복소환기이고; R1은 수소 또는 할로겐이고; R2는 단일결합, 알킬렌, 또는 티아알킬렌이고; R3는 수소원자, 염형성원자 또는 기, 또는 에스테르 형성기이고; R4는 수소 또는 메톡시이고; R5는 수소 또는 세팔로스포린의 3-치환기이고; R6는 수소원자, 염형성 원자 또는 기, 또는 에스테르 형성기이고; X는 산소, 황, 또는 술피닐이며, 단 R이 티아알킬렌일때 R1은 할로겐이다.)
- 하기 일반식(Ⅰ)로 표시되는 R, R3, R5및 R6중 최소한 하나가 보호된 7베타-(카르복시알케노 일아미노)-3-세펨-4-카르복시산 또는 그의 반응성 유도체의 보호 아미노 또는 보호 카르복시를 공지의 방법으로 탈보호시킴을 특징으로 하기 일반식(Ⅰ)로 표시되는 화합물의 제조방법.(상기 식중, R은 아릴 또는 복소환기이고; R1은 수소 또는 할로겐이고; R2는 단일결합, 알킬렌, 또는 티아알킬렌이고; R3는 수소원자, 염형성원자 또는 기, 또는 에스테르 형성기이고; R4는 수소 또는 메톡시이고; R5는 수소 또는 세팔로스포린의 3-치환기이고; R6는 수소원자, 염형성 원자 또는 기, 또는 에스테르 형성기이고; X는 산소, 황, 또는 술피닐이며, 단 R이 티아알킬렌일 때 R1은 할로겐이다.)
- 하기 일반식(Ⅷ)의 옥살레이트를 불활성 용매내에서 50℃~120℃온도로 10분~10시간 동안에 하기 일반식(Ⅸ)의 알킬리덴포스포란으로 처리함으로써 비티히 반응시킴을 특징으로하는 하기 일반식(Ⅶ)의 화합물의 제조방법.(상기 식중, R은 아릴 또는 복소환기이고; R1은 수소 또는 할로겐이고; R2는 단일결합, 알킬렌, 또는 티아알킬렌이고; R3는 수소원자, 염형성원자 또는 기, 또는 에스테르 형성기이고; R6는 수소원자, 염형성 원자 또는 기, 또는 에스테르 형성기이고; Ar은 아릴이며, 단 R이 티아알킬렌일 때 R1은 할로겐이다.)
- 하기 일반식(Ⅳ)의 포르밀 옥살레이트 또는 그의 아세탈을 불활성 용매내에서 50℃~120℃의 온도로 10분~10시간동안에 하기 일반식(Ⅴ)의 알킬리덴 포스포란으로 처리함으로써 비티히 반응시킴을 특징으로 하는 하기 일반식(Ⅶ)의 화합물의 제조방법.(상기 식중, R은 아릴 또는 복소환기이고; R1은 수소 또는 할로겐이고; R2는 단일결합, 알킬렌, 또는 티아알킬렌이고; R3는 수소원자, 염형성 원자 또는 기, 또는 에스테르 형성기이고; R6는 수소원자, 염형성 원자 또는 기 또는 에스테르 형성기이고; R20은 단일결합 또는 1~3C알킬렌이고; Ar은 아릴이며, 단 R이 티아알킬렌일 때 R1은 할로겐이다.)
- 카르복시 보호기 R3또는 R6를 불활성 용매 내에서 -50℃~100℃ 온도로 1/6~10시간 동안에 산 루이스산 및 양이온 스캐빈저, 염기, 또는 수소 및 촉매로 처리함으로써 탈보호시킴을 특징으로 하는 R3및 R6중 하나 또는 둘다가 수소인 하기 일반식(Ⅶ)의 화합물의 제조방법.(상기 식중, R은 아릴 또는 복소환기이고; R1은 수소 또는 할로겐이고; R2는 단일결합, 알킬렌, 또는 티아알킬렌이고; R3는 수소원자, 염형성 원자 또는 기, 또는 에스테르 형성기이고; R6는 수소원자, 염형성원자 또는 기, 또는 에스테르 형성기이고; 단, R이 티아알킬렌일 때 R1은 할로겐이고, R3및 R6중 최소한 하나는 수소이다.)※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019880012223A KR880002684B1 (ko) | 1983-10-04 | 1988-09-21 | 카르복시알켄산 및 그의 유도체의 제조방법 |
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58186601A JPS6078987A (ja) | 1983-10-04 | 1983-10-04 | アクリルアミドセフアロスポリン類 |
| JP186601 | 1983-10-04 | ||
| JP186601/83 | 1983-10-04 | ||
| JP18563/84 | 1984-02-03 | ||
| JP59018563A JPS60163884A (ja) | 1984-02-03 | 1984-02-03 | カルボキシアルケンアミドセフアロスポリン |
| JP18563 | 1984-02-03 | ||
| JP59100890A JPH0780892B2 (ja) | 1984-05-18 | 1984-05-18 | カルボキシアルケンアミドセフアロスポリン |
| JP100890 | 1984-05-18 | ||
| JP100890/84 | 1984-05-18 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019880012223A Division KR880002684B1 (ko) | 1983-10-04 | 1988-09-21 | 카르복시알켄산 및 그의 유도체의 제조방법 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR850002989A true KR850002989A (ko) | 1985-05-28 |
| KR880002376B1 KR880002376B1 (ko) | 1988-11-03 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840006134A KR880002376B1 (ko) | 1983-10-04 | 1984-10-04 | 카르복시 알켄아미도 세팔로스포린의 제조방법 |
| KR1019880012223A KR880002684B1 (ko) | 1983-10-04 | 1988-09-21 | 카르복시알켄산 및 그의 유도체의 제조방법 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019880012223A KR880002684B1 (ko) | 1983-10-04 | 1988-09-21 | 카르복시알켄산 및 그의 유도체의 제조방법 |
Country Status (22)
| Country | Link |
|---|---|
| US (3) | US4634697A (ko) |
| EP (1) | EP0136721B1 (ko) |
| KR (2) | KR880002376B1 (ko) |
| AR (1) | AR242392A1 (ko) |
| AT (1) | ATE99311T1 (ko) |
| AU (2) | AU575854B2 (ko) |
| CA (2) | CA1238910A (ko) |
| DE (2) | DE3486259T2 (ko) |
| DK (1) | DK171043B1 (ko) |
| ES (3) | ES8604602A1 (ko) |
| FI (1) | FI82057C (ko) |
| GB (3) | GB2154580B (ko) |
| GR (1) | GR80544B (ko) |
| HU (1) | HU193298B (ko) |
| IE (1) | IE57744B1 (ko) |
| IL (3) | IL84653A (ko) |
| MX (1) | MX174328B (ko) |
| NL (1) | NL940013I2 (ko) |
| NO (2) | NO173238C (ko) |
| NZ (2) | NZ218741A (ko) |
| PH (2) | PH20223A (ko) |
| PT (1) | PT79287A (ko) |
Families Citing this family (75)
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| AU575854B2 (en) * | 1983-10-04 | 1988-08-11 | Shionogi & Co., Ltd. | 7beta-(carboxyalkenamido) cephalosporins |
| JP2501785B2 (ja) * | 1984-07-09 | 1996-05-29 | 明治製菓株式会社 | 新規セフアロスポリン系化合物 |
| JPS6124580A (ja) * | 1984-07-12 | 1986-02-03 | Shionogi & Co Ltd | アミノチアゾリルグルタル酸誘導体の製造方法 |
| JPS6153272A (ja) * | 1984-08-24 | 1986-03-17 | Shionogi & Co Ltd | グルタル酸誘導体の製法 |
| AU580855B2 (en) * | 1985-03-29 | 1989-02-02 | Shionogi & Co., Ltd. | Alkeneamidocephalosporin esters |
| EP0202046B1 (en) | 1985-04-30 | 1991-01-30 | Eli Lilly And Company | 7-substituted bicyclic pyrazolidinones |
| US4731362A (en) * | 1985-08-05 | 1988-03-15 | Shionogi & Co., Ltd. | Alkylcarbamoyloxymethylcephem compounds |
| DE3745094B4 (de) * | 1986-07-02 | 2004-12-30 | Shionogi & Co., Ltd. | Ein kristallines Hydrat der 7ß-[(Z)-2-(2-Aminothiazol-4-yl)-4-carboxybut-2-enoylamino]-3-cephem-4-carbonsäure enthaltende Hartgelatinekapsel-Zusammensetzung |
| NZ220764A (en) * | 1986-07-02 | 1989-09-27 | Shionogi & Co | Crystalline form of 7beta((z)-2-(2-aminothiazol-4-yl)-4- carboxybut-2-enoylamino)-3-cephem-4-carboxylic acid and pharmaceutical compositions |
| US5017380A (en) * | 1986-07-02 | 1991-05-21 | Shionogi & Co., Ltd. | Gelatin hard capsule containing crystalline hydrate of oral cephalosporin |
| AT396652B (de) * | 1986-07-02 | 1993-11-25 | Shionogi & Co | Verfahren zur herstellung von hartgelatinekapsel-zusammensetzungen |
| US5147871A (en) * | 1986-07-03 | 1992-09-15 | Hoffmann La-Roche, Inc. | Anti-bacterial cephalosporin compounds |
| US5242913A (en) * | 1987-03-11 | 1993-09-07 | Pfizer Inc. | Substituted 3-cephem compounds as antibacterial agents |
| US5079242A (en) * | 1987-03-11 | 1992-01-07 | Pfizer Inc. | Substituted 3-cephem compounds as antibacterial agents |
| US4820832A (en) * | 1988-03-23 | 1989-04-11 | Eli Lilly And Company | Process for preparing 3-unsubstituted cephalosporins and 1-carba(dethia)cephalosporins |
| CS273349B2 (en) * | 1988-03-31 | 1991-03-12 | Hoffmann La Roche | Method of cephalosporin's new derivatives production |
| US5336768A (en) * | 1988-05-24 | 1994-08-09 | Hoffmann-La Roche Inc. | Antibacterial cephalosporin compounds |
| US5245027A (en) * | 1989-11-21 | 1993-09-14 | Bristol-Myers Squibb Company | 3-fluorosulfonyloxyceph-3-em compounds |
| US5612048A (en) * | 1994-11-22 | 1997-03-18 | Amvac Chemical Corporation | Stabilized moisture-sensitive pesticide composition and method of making |
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| JPH101482A (ja) * | 1996-06-13 | 1998-01-06 | Otsuka Chem Co Ltd | ３−ノルセフェム化合物の製造法 |
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| CA2533292C (en) * | 2003-07-21 | 2013-12-31 | Advancis Pharmaceutical Corporation | Antibiotic product, use and formulation thereof |
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| WO2005023184A2 (en) * | 2003-08-29 | 2005-03-17 | Advancis Pharmaceuticals Corporation | Antibiotic product, use and formulation thereof |
| WO2005027877A1 (en) * | 2003-09-15 | 2005-03-31 | Advancis Pharmaceutical Corporation | Antibiotic product, use and formulation thereof |
| EP1701705A4 (en) * | 2003-12-24 | 2007-08-08 | Advancis Pharmaceutical Corp | IMPROVED ABSORPTION OF MODIFIED RELEASE DOSAGE FORMS |
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| US20110104109A1 (en) * | 2005-07-13 | 2011-05-05 | Frank Bennett | Tetracyclic indole derivatives and their use for treating or preventing viral infections |
| US8778924B2 (en) * | 2006-12-04 | 2014-07-15 | Shionogi Inc. | Modified release amoxicillin products |
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| CN102159579B (zh) * | 2008-06-13 | 2015-03-25 | 默沙东公司 | 三环吲哚衍生物及其使用方法 |
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| EP2755981A4 (en) | 2011-09-14 | 2015-03-25 | Merck Sharp & Dohme | HETEROCYCLIC COMPOUNDS CONTAINING SILYL AND METHODS OF USING THE SAME FOR TREATING VIRAL DISEASES |
| WO2013109225A1 (en) | 2012-01-18 | 2013-07-25 | Mahmut Bilgic | Pharmaceutical tablet formulations comprising ceftibuten |
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| GB149039A (en) * | 1919-04-30 | 1920-07-30 | Lawrence Ennis | Improvements in or relating to steel framed cottages |
| GB966131A (en) * | 1959-04-07 | 1964-08-06 | Union Carbide Corp | Process for the preparation of organic compounds |
| US3994888A (en) * | 1973-06-18 | 1976-11-30 | Eli Lilly And Company | Cephalosporin cleavage process |
| GB1497039A (en) * | 1973-12-05 | 1978-01-05 | Glaxo Lab Ltd | Penicillins and cephalosporins |
| US4263212A (en) * | 1979-02-28 | 1981-04-21 | Rikagaku Kenkyusho | Process for preparation of substituted olefins |
| GB2076801A (en) * | 1980-04-14 | 1981-12-09 | Erba Farmitalia | alpha , beta -Disubstituted Acrylamido Cephalosporins |
| DE3037997A1 (de) * | 1980-10-08 | 1982-05-13 | Bayer Ag | (beta) -lactamantibiotika, verfahren zu deren herstellung sowie sie enthaltende mittel |
| DE3145727A1 (de) * | 1981-11-19 | 1983-05-26 | Bayer Ag, 5090 Leverkusen | Zwischenprodukte, verfahren zu deren herstellung und verfahren zur herstellung von cephalosporinen |
| CA1201431A (en) * | 1981-12-17 | 1986-03-04 | Daiei Tunemoto | .beta.-LACTAM COMPOUNDS, PROCESS FOR THE PREPARATION THEREOF AND INTERMEDIATE PRODUCTS FOR THE PREPARATION THEREOF |
| DE3224866A1 (de) * | 1982-07-02 | 1984-01-05 | Bayer Ag, 5090 Leverkusen | Ss-lactamantibiotika, verfahren zu deren herstellung sowie sie enthaltende mittel |
| DE3300593A1 (de) * | 1983-01-11 | 1984-07-12 | Bayer Ag, 5090 Leverkusen | Neue cephalosporine und verfahren zu ihrer herstellung |
| AU575854B2 (en) * | 1983-10-04 | 1988-08-11 | Shionogi & Co., Ltd. | 7beta-(carboxyalkenamido) cephalosporins |
-
1984
- 1984-09-19 AU AU33300/84A patent/AU575854B2/en not_active Expired
- 1984-09-21 NZ NZ218741A patent/NZ218741A/xx unknown
- 1984-09-21 NZ NZ209634A patent/NZ209634A/xx unknown
- 1984-09-25 PH PH31265A patent/PH20223A/en unknown
- 1984-09-27 CA CA000464215A patent/CA1238910A/en not_active Expired
- 1984-10-01 PT PT79287A patent/PT79287A/pt unknown
- 1984-10-02 NO NO843956A patent/NO173238C/no not_active IP Right Cessation
- 1984-10-02 FI FI843871A patent/FI82057C/fi not_active IP Right Cessation
- 1984-10-03 DK DK474584A patent/DK171043B1/da not_active IP Right Cessation
- 1984-10-03 GB GB08424923A patent/GB2154580B/en not_active Expired
- 1984-10-03 IE IE2524/84A patent/IE57744B1/en not_active IP Right Cessation
- 1984-10-03 HU HU843743A patent/HU193298B/hu unknown
- 1984-10-03 GR GR80544A patent/GR80544B/el unknown
- 1984-10-03 MX MX013280A patent/MX174328B/es unknown
- 1984-10-04 AR AR84298181A patent/AR242392A1/es active
- 1984-10-04 EP EP84111916A patent/EP0136721B1/en not_active Expired - Lifetime
- 1984-10-04 AT AT84111916T patent/ATE99311T1/de active
- 1984-10-04 IL IL84653A patent/IL84653A/xx not_active IP Right Cessation
- 1984-10-04 KR KR1019840006134A patent/KR880002376B1/ko not_active IP Right Cessation
- 1984-10-04 DE DE3486259T patent/DE3486259T2/de not_active Expired - Lifetime
- 1984-10-04 DE DE198484111916T patent/DE136721T1/de active Pending
- 1984-10-04 IL IL73159A patent/IL73159A/xx not_active IP Right Cessation
- 1984-10-04 ES ES536502A patent/ES8604602A1/es not_active Expired
-
1985
- 1985-03-12 US US06/711,017 patent/US4634697A/en not_active Expired - Lifetime
- 1985-08-29 ES ES547300A patent/ES8700222A1/es not_active Expired
- 1985-08-29 ES ES547301A patent/ES8605278A1/es not_active Expired
- 1985-09-27 NO NO853806A patent/NO176567C/no not_active IP Right Cessation
-
1986
- 1986-02-20 US US06/831,435 patent/US4748170A/en not_active Expired - Lifetime
- 1986-05-27 PH PH33818A patent/PH21766A/en unknown
-
1987
- 1987-01-06 GB GB08700123A patent/GB2190914B/en not_active Expired
- 1987-03-04 CA CA000531176A patent/CA1272713A/en not_active Expired - Lifetime
- 1987-11-13 GB GB08726623A patent/GB2198727B/en not_active Expired
- 1987-11-27 IL IL84653A patent/IL84653A0/xx unknown
- 1987-12-09 US US07/132,882 patent/US4912224A/en not_active Expired - Lifetime
-
1988
- 1988-05-16 AU AU16194/88A patent/AU601842B2/en not_active Expired
- 1988-09-21 KR KR1019880012223A patent/KR880002684B1/ko not_active IP Right Cessation
-
1994
- 1994-07-04 NL NL940013C patent/NL940013I2/nl unknown
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