KR840009116A - 세펨화합물의 제조방법 - Google Patents
세펨화합물의 제조방법 Download PDFInfo
- Publication number
- KR840009116A KR840009116A KR1019840002447A KR840002447A KR840009116A KR 840009116 A KR840009116 A KR 840009116A KR 1019840002447 A KR1019840002447 A KR 1019840002447A KR 840002447 A KR840002447 A KR 840002447A KR 840009116 A KR840009116 A KR 840009116A
- Authority
- KR
- South Korea
- Prior art keywords
- optionally substituted
- group
- alkyl
- formula
- substituted
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 6
- 238000004519 manufacturing process Methods 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003302 alkenyloxy group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000005133 alkynyloxy group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- -1 deca-methylene Chemical group 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-O isoquinolin-2-ium Chemical compound C1=[NH+]C=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-O 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
- C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (2)
- 일반식(Ⅱ)의 화합물을 트리-C1내지 4-알킬-요도실란의 존재하에서 A에 상응하는 염기와 반응시켜, 일반식(Ⅲ)의 화합물을 생성시키고, 아미노-보호그룹이 존재하는 경우에는 보호그룹을 제거한후, R8이 수소인 일반식(Ⅲ)의 화합물을 그대로 또는 그의 반응성 유도체 형태로 일반식(Ⅳ)의 2-씬옥시이미노 아세트산 또는 카보닐그룹이 활성화된 일반식(Ⅳ)화합물의 유도체와 반응시킴을 특징으로 하여, 일반식(Ⅰ)의 화합물을 제조하는 방법.상기식에서R은 티아졸릴라디탈또는 1,2,4-티아디아졸라디칼(여기서, R3은 수소 /또는 할로겐이고, B는 임의로 치환된 아미노 그룹이다)이고;R1은 수소 또는 메톡시이며;R2은 수소, 임의로 치환된 C1내지 6-알킬, 임의로 치환된 C2내지 6-알케닐, C2내지 6-알키닐-C3내지 7-이클로알킬, C3내지 7-사이클로알킬-C1내지 6-알킬, C4내지 7-사이클로알케닐 또는 mR6그룹(여기서 m 및 n은 각각 0또는 1이고, R4및 R5는 동일 또는 상이하고, 수소, 아릴 또는 C1내지 4-알킬 그룹을 나타내거나 R4및 R5가 이들이 결합된 탄소와함께는 메텔렌 또는 C3내지 7-사이클로알킬리덴은 또한 일치환 또는 다치환될 수 있으며 R6는 COOH,CN 또는 CONH2그룹을 나타내고, 여기에서 CONH2-그룹은 질소상에서 일치환 또는 이치환될 수있다)이고;A는 퀴논리늄또는 이소퀴놀리늄라디칼(이들은 또한 각각, 임의로 치환된 C1내지 6-알킬, C1내지 6-알콕시, 할로겐, 트리플루오로메틸 및 하이드록시 그룹중에서 선택한 동일 또는 상이한 치환기에 의해 일 또는 다 치환될 수 있다)이거나, 펜안트리디늄라디칼이거나, 또는 임의로 치환된 C2내지 6-알킬(이 경우에는 오르토-위치에 있는 2개의 알킬그룹이 결합되어 임의로 치환된다-내지 데카-메틸렌환을 형성할 수 있으며, 여기서 환중의 하나의 탄소원자가 헤테로원자로 치환될 수 있고, 또한 하나 또는 두개의 이중결합을 함유할 수도 있다.) 임의로 치환된 C2내지 6-알케닐, C2내지 6-알키닐, C3내지 7-사이클로알킬 및 C3내지 7-사이클로알킬메틸,(여기서, 사이클로알킬 및 사이클로알킬메틸 치환기에서는 환이 또한 치환될 수 있다), C4내지 7-사이클로알케닐, 임의로 치환된 C1내지 6-알콕시, C2내지 6-알케닐옥시 및 C2내지 6-알키닐옥시, 할로겐, 트리플루오로메틸 및 하이드록시, 임의로 치환된 페닐, 벤질 및 헤테로아릴, 포로밀 및 케탈환된 포르밀, 임의로 치환된 C1내지 6-알킬카보닐(이것은 또한 케탈환된 형태일수 있다), 아릴카보닐 및 카바모일 그룹중 선택한 동일 또는 상이한 치환기로 일 또는 다 치환될 수 있는 피리디늄 라디칼이고;R2O그룹은 씬-위치에 있으며;R7은 일반식(Ⅰ)의 라디칼 A에 상응하는 염기로 치환될 수 있는 그룹을 나타내고;R8은 수소 또는 아미노-보호그룹을 나타낸다.
- 제1항에 있어서, 트리-C1내지 4-알킬요도실란이 트리메틸 -또는 트리에틸-요도실란임을 특징으로 하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19833316798 DE3316798A1 (de) | 1983-05-07 | 1983-05-07 | Verfahren zur herstellung von cephemverbindungen |
DEP3316798.2 | 1983-05-07 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR840009116A true KR840009116A (ko) | 1984-12-24 |
KR910004332B1 KR910004332B1 (ko) | 1991-06-26 |
Family
ID=6198462
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019840002447A KR910004332B1 (ko) | 1983-05-07 | 1984-05-04 | 세펨화합물의 제조방법 |
Country Status (24)
Country | Link |
---|---|
US (1) | US4667028A (ko) |
EP (1) | EP0124889A3 (ko) |
JP (1) | JPS6034972A (ko) |
KR (1) | KR910004332B1 (ko) |
AU (1) | AU575825B2 (ko) |
CA (1) | CA1224457A (ko) |
CS (1) | CS247081B2 (ko) |
DD (1) | DD251133A5 (ko) |
DE (1) | DE3316798A1 (ko) |
DK (1) | DK166282C (ko) |
ES (1) | ES8502445A1 (ko) |
FI (1) | FI82055C (ko) |
HU (1) | HU191683B (ko) |
IL (1) | IL71771A (ko) |
MA (1) | MA20110A1 (ko) |
MT (1) | MTP947B (ko) |
MX (1) | MX168599B (ko) |
NO (1) | NO841792L (ko) |
NZ (1) | NZ208064A (ko) |
OA (1) | OA07766A (ko) |
PH (1) | PH19554A (ko) |
PT (1) | PT78544B (ko) |
YU (1) | YU45965B (ko) |
ZA (1) | ZA843343B (ko) |
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS60169486A (ja) * | 1984-02-10 | 1985-09-02 | Yamanouchi Pharmaceut Co Ltd | 7−アミノ−3−置換メチル−3−セフエム−4−カルボン酸およびその低級アルキルシリル誘導体の製造法 |
IL74822A (en) * | 1984-04-17 | 1989-06-30 | Daiichi Seiyaku Co | Cephalosporin derivatives and salts thereof and their preparation |
US4788185A (en) * | 1984-04-23 | 1988-11-29 | Takeda Chemical Industries, Ltd. | Cephalosporin compounds |
ATE121746T1 (de) * | 1984-11-23 | 1995-05-15 | Biochemie Gmbh | Verfahren zur herstellung bissilylierter 3- iodmethylcephalosporinderivaten. |
ATE89826T1 (de) * | 1985-03-01 | 1993-06-15 | Takeda Chemical Industries Ltd | Antibakterielle verbindungen, ihre herstellung und verwendung. |
US4703118A (en) * | 1985-04-08 | 1987-10-27 | Eli Lilly And Company | Synthesis of 3-iodomethyl cephalosporins |
GB8519606D0 (en) * | 1985-08-05 | 1985-09-11 | Fujisawa Pharmaceutical Co | 3 7-d substituted-3-cephem compounds |
US4714760A (en) * | 1985-08-20 | 1987-12-22 | Bristol-Myers Company | Cephalosporin intermediates |
US4749522A (en) * | 1985-10-31 | 1988-06-07 | Angio-Medical Corporation | Supercritical fluid extraction of animal derived materials |
DE3542644A1 (de) * | 1985-12-03 | 1987-06-04 | Hoechst Ag | Verfahren zur herstellung von cefodizim |
CA1296012C (en) * | 1986-03-19 | 1992-02-18 | Susumu Nakagawa | 6,7-dihydroxy-isoquinoline derivatives |
US4868294A (en) * | 1986-07-11 | 1989-09-19 | Bristol-Myers Company | Process for preparing cephalosporin intermediates |
DE3706020A1 (de) * | 1987-02-25 | 1988-09-08 | Hoechst Ag | Kristallisierte cephem-saeureadditionssalze und verfahren zu ihrer herstellung |
TWI335332B (en) * | 2001-10-12 | 2011-01-01 | Theravance Inc | Cross-linked vancomycin-cephalosporin antibiotics |
CN102002058B (zh) * | 2010-11-05 | 2012-04-04 | 山东鲁抗立科药物化学有限公司 | 硫酸头孢喹肟的合成方法 |
EP2862569A1 (en) | 2011-09-09 | 2015-04-22 | Cubist Pharmaceuticals, Inc. | Methods for treating intrapulmonary infections |
US8809314B1 (en) | 2012-09-07 | 2014-08-19 | Cubist Pharmacueticals, Inc. | Cephalosporin compound |
US8476425B1 (en) | 2012-09-27 | 2013-07-02 | Cubist Pharmaceuticals, Inc. | Tazobactam arginine compositions |
US9872906B2 (en) | 2013-03-15 | 2018-01-23 | Merck Sharp & Dohme Corp. | Ceftolozane antibiotic compositions |
KR102226197B1 (ko) | 2013-03-15 | 2021-03-11 | 머크 샤프 앤드 돔 코포레이션 | 세프톨로잔 항균성 조성물 |
US9320740B2 (en) | 2013-03-15 | 2016-04-26 | Merck Sharp & Dohme Corp. | Ceftolozane-tazobactam pharmaceutical compositions |
WO2015035376A2 (en) | 2013-09-09 | 2015-03-12 | Calixa Therapeutics, Inc. | Treating infections with ceftolozane/tazobactam in subjects having impaired renal function |
US20150094293A1 (en) | 2013-09-27 | 2015-04-02 | Calixa Therapeutics, Inc. | Solid forms of ceftolozane |
CN103601738A (zh) * | 2013-12-04 | 2014-02-26 | 哈药集团制药总厂 | 一种头孢匹罗氢碘酸盐的制备方法 |
CN105646543B (zh) * | 2016-03-17 | 2018-03-27 | 天津大学 | 一种头孢喹肟晶体及其制备方法 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AR228726A1 (es) * | 1978-05-26 | 1983-04-15 | Glaxo Group Ltd | Procedimiento para la preparacion del antibiotico(6r,7r)-7-((z)-2-(2-aminotiazol-4-il)-2-(2-carboxiprop-2-oxiimino)acetamido)-3-(1-piridiniometil)cef-3-em-4-carboxilato |
US4266049A (en) * | 1980-02-20 | 1981-05-05 | Eli Lilly And Company | Process for 3-iodomethyl cephalosporins |
US4367228A (en) * | 1980-10-29 | 1983-01-04 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compound and composition |
US4336253A (en) * | 1981-03-11 | 1982-06-22 | Eli Lilly And Company | Cephalosporin antibiotics |
DE3118732A1 (de) * | 1981-05-12 | 1982-12-02 | Hoechst Ag, 6000 Frankfurt | Cephalosporinderivate und verfahren zu ihrer herstellung |
ZA825095B (en) * | 1981-07-17 | 1983-05-25 | Glaxo Group Ltd | Cephalosporin compounds |
US4396619A (en) * | 1981-09-08 | 1983-08-02 | Eli Lilly And Company | Cephalosporin betaines |
ZA826538B (en) * | 1981-09-08 | 1984-04-25 | Lilly Co Eli | Thieno and furopyridinium-substituted cephalosporin derivatives |
US4396620A (en) * | 1981-09-08 | 1983-08-02 | Eli Lilly And Company | Cephalosporin quinolinium betaines |
US4402955A (en) * | 1981-10-02 | 1983-09-06 | Eli Lilly And Company | Dioximino cephalosporin antibiotics |
-
1983
- 1983-05-07 DE DE19833316798 patent/DE3316798A1/de not_active Withdrawn
-
1984
- 1984-04-27 YU YU76684A patent/YU45965B/sh unknown
- 1984-05-02 HU HU841704A patent/HU191683B/hu not_active IP Right Cessation
- 1984-05-03 MT MT947A patent/MTP947B/xx unknown
- 1984-05-03 FI FI841764A patent/FI82055C/fi not_active IP Right Cessation
- 1984-05-03 MA MA20331A patent/MA20110A1/fr unknown
- 1984-05-04 AU AU27705/84A patent/AU575825B2/en not_active Ceased
- 1984-05-04 CS CS843303A patent/CS247081B2/cs unknown
- 1984-05-04 DK DK224284A patent/DK166282C/da active
- 1984-05-04 DD DD84262706A patent/DD251133A5/de not_active IP Right Cessation
- 1984-05-04 KR KR1019840002447A patent/KR910004332B1/ko not_active Application Discontinuation
- 1984-05-04 PT PT78544A patent/PT78544B/pt unknown
- 1984-05-04 ES ES532183A patent/ES8502445A1/es not_active Expired
- 1984-05-04 EP EP84105025A patent/EP0124889A3/de not_active Withdrawn
- 1984-05-04 ZA ZA843343A patent/ZA843343B/xx unknown
- 1984-05-04 NO NO841792A patent/NO841792L/no unknown
- 1984-05-04 MX MX007999A patent/MX168599B/es unknown
- 1984-05-04 CA CA000453602A patent/CA1224457A/en not_active Expired
- 1984-05-04 US US06/607,403 patent/US4667028A/en not_active Expired - Fee Related
- 1984-05-04 NZ NZ208064A patent/NZ208064A/en unknown
- 1984-05-06 IL IL71771A patent/IL71771A/xx unknown
- 1984-05-07 OA OA58291A patent/OA07766A/xx unknown
- 1984-05-07 PH PH30651A patent/PH19554A/en unknown
- 1984-05-07 JP JP59090842A patent/JPS6034972A/ja active Pending
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