HK3392A - Intermediates and process for antibiotics - Google Patents

Intermediates and process for antibiotics

Info

Publication number
HK3392A
HK3392A HK33/92A HK3392A HK3392A HK 3392 A HK3392 A HK 3392A HK 33/92 A HK33/92 A HK 33/92A HK 3392 A HK3392 A HK 3392A HK 3392 A HK3392 A HK 3392A
Authority
HK
Hong Kong
Prior art keywords
group
formula
amino
alkyl
hydrogen
Prior art date
Application number
HK33/92A
Other languages
English (en)
French (fr)
Inventor
David Albert Evans
Eric Brian Sjogren
Original Assignee
President And Fellows Of Harvard College
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by President And Fellows Of Harvard College filed Critical President And Fellows Of Harvard College
Publication of HK3392A publication Critical patent/HK3392A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D463/00—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D463/10—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with 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
    • C07D463/14—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with 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 with hetero atoms directly attached in position 7
    • C07D463/16—Nitrogen atoms
    • C07D463/18—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof
    • C07D463/20—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof with the acylating radicals further substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • 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
    • C07D463/00—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D463/00—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D463/10—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with 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
    • C07D463/14—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with 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 with hetero atoms directly attached in position 7
    • C07D463/16—Nitrogen atoms
    • C07D463/18—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof
    • C07D463/20—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof with the acylating radicals further substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D463/22—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof with the acylating radicals further substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen further substituted by nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Communicable Diseases (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Cephalosporin Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Claims (10)

1. Eine Verbindung der Formel (1):
worin A Wasserstoff, eine Amino-Schutzgruppe oder eine Acylgruppe ist, worin R Wasserstoff, C1-C6-Alkyl, Ci-C6-Alkyl, substituiert durch Cyano, Carboxy, Halogen, Amino, C1-C4-Alkoxy, C1-C4-Alkylthio oder Trifluormethyl, ist; eine Phenyl- oder substituierte Phenylgruppe, die durch die folgende Formel wiedergegeben ist worin a und a' unabhängig voneinander Wasserstoff, Halogen, Hydroxy, C1-C4-Alkoxy, C1-C4-Alkanoyloxy, C1-C4-Alkyl, C1-C4-Alkylthio, Amino, C1-C4-Alkanoylamino, C1-C4-Alkylulfonylamino, Carboxy, Carbamoyl, Hydroxymethyl, Aminomethyl oder Carboxymethyl sind; eine Gruppe der Formelworin a und a' die gleiche Bedeutung wie oben festgelegt haben, Z O oder S und m 0 oder 1 ist; eine Heteroarylmethylgruppe der Formel R1-CH2-, worin R1 Thienyl, Furyl, Benzothienyl, Benzofuryl, Indolyl, Triazolyl, Tetrazolyl, Oxazolyl, Thiazolyl, Oxadiazolyl, Thiadiazolyl und solche durch Amino, Hydroxy, Halogen, C1-C4-Alkyl oder C1-C4-Alkoxy oder C1-C4-Alkylsulfonylamino substituierte Heteroarylgruppe ist; eine substituierte Methylgruppe der Formel worin R2 Cyclohex-1,4-dienyl oder eine Phenylgruppe oder substituierte Phenylgruppe der Formel ist, worin a und a' die gleiche wie oben festgelegte Bedeutung haben oder R2 R1 wie oben festgelegt, bedeutet und Q Hydroxy, Ct-C4-Alkanoyloxy, Carboxy, Sulfo, Amino oder eine substituierte Aminogruppe der Formel ist, worin R' Wasserstoff oder Ci-C4-Alkyl ist, und R" C1-C4-Alkyl, Furyl, Thienyl, Phenyl, Halogenphenyl, Nitrophenyl, Styryl, Halogenstyryl, Nitrostyryl ist oder eine Gruppe worin R' die oben festgelegte Bedeutung hat und R"' Wasserstoff, C1-C3-Alkylsulfonyl, C1-C3-Alkyl oder C1-C4-Alkanoyl ist; oder Q ist eine Gruppe der Formel worin R"' die oben festgelegte Bedeutung hat, und q 2 oder 3 ist; oder Q ist eine Gruppe der Formel oder Q ist eine Benzamidogruppe der Formel worin t 1 bis 3 ist; oder R ist eine Ketogruppe oder eine Oximinogruppe der Formeln worin R3 R1 oder R2, wie oben festgelegt, ist, und R4 Wasserstoff, C1-C4-Alkyl oder ein carboxysubstituiertes Alkyl oder Cycloalkyl der Formel ist, worin b und b' unabhängig voneinander Wasserstoff oder C1-C3-Alkyl sind oder gemeinsam mit dem Kohlenstoffatom, an das sie gebunden sind, einen drei- bis sechsgliedrigen Kohlenstoffring bilden, und R5 Hydroxy, C1-C4-Alkoxy, Amino, C1-C4-Alkylamino oder Di-(C1-C4-alkyl)-amino ist; R2 ist Wasserstoff oder eine Carboxy-Schutzgruppe oder falls R2 Wasserstoff ist, ein Salz davon.
2. Eine Verbindung nach Anspruch 1, worin R eine Gruppe der Formel ist.
3. Eine Verbindung nach Anspruch 2, worin R Phenoxymethyl oder Benzyl ist.
4. Eine Verbindung nach Anspruch 1, worin R eine Ketogruppe oder eine Oximinogruppe der Formel ist.
5. Eine Verbindung nach Anspruch 4, worin R3 2-Aminothiazol-4-yl ist. 6. Verfahren zur Herstellung einer Verbindung der Formel 1, wie sie in einem der Ansprüche 1 bis 5 beansprucht wird, enthaltend die 0-Acylierung einer Verbindung der Formel worin A etwas anderes als Wasserstoff ist, mit einer aktivierten Form der Trifluormethansulfonsäure.
7. Ein Verfahren zur Herstellung einer 3-Halogen-1-carba-3-cephem-Verbindung der Formel (4):worin A und R2 die in Anspruch 1 festgelegte Bedeutung hat und X" Chlor oder Brom ist, enthaltend das Ersetzen der Triflatestergruppe einer Verbindung der Formel (1): mit einem Chlorid- oder Bromidion, gegebenenfalls soweit erwünscht, gefolgt durch die Entfernung eines Esters (R2) und/oder einer Amino-Schutzgruppe (A) und/oder Acylierung des 7-Amino-Anteils, in dem A Wasserstoff ist, zur Herstellung einer Verbindung, worin A RCO ist.
8. Ein Verfahren nach Anspruch 7, worin die Chlorid- und Bromidionen aus Lithiumchlorid oder -bromid erhalten werden.
9. Ein Verfahren nach Anspruch 7 oder 8 zur Herstellung einer Verbindung der Formel: enthaltend die Acylierung einer Verbindung der Formel mit D-Phenylglycin oder einem aktivierten oder geschützten Derivat davon, und nachfolgender Entfernung einer vorhandenen Amino- oder Esterschutzgruppe.
HK33/92A 1985-08-02 1992-01-09 Intermediates and process for antibiotics HK3392A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US06/761,647 US4673737A (en) 1985-08-02 1985-08-02 7-acylamino-(or 7-amino)-3-trifluoromethylsulfonyloxy-1-carba(1-dethia)-3-cephem-4-carboxylic acids and esters thereof

Publications (1)

Publication Number Publication Date
HK3392A true HK3392A (en) 1992-01-17

Family

ID=25062866

Family Applications (1)

Application Number Title Priority Date Filing Date
HK33/92A HK3392A (en) 1985-08-02 1992-01-09 Intermediates and process for antibiotics

Country Status (22)

Country Link
US (1) US4673737A (de)
EP (1) EP0211540B1 (de)
JP (2) JPH0762016B2 (de)
KR (1) KR900001883B1 (de)
CN (1) CN1015103B (de)
AT (1) ATE52779T1 (de)
AU (1) AU586694B2 (de)
CA (2) CA1262356A (de)
DE (1) DE3671225D1 (de)
DK (1) DK335786A (de)
ES (1) ES2000589A6 (de)
GR (1) GR861858B (de)
HK (1) HK3392A (de)
HU (1) HU201932B (de)
IE (1) IE58998B1 (de)
IL (1) IL79421A (de)
NZ (1) NZ216872A (de)
PH (1) PH22722A (de)
PT (1) PT82990B (de)
SG (1) SG78091G (de)
SU (1) SU1547709A3 (de)
ZA (1) ZA865275B (de)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4665171A (en) 1985-07-17 1987-05-12 Harvard University Process and intermediates for β-lactam antibiotics
US4820816A (en) * 1985-08-02 1989-04-11 President And Fellows Of Harvard College 3-trifuoromethylsulfonyloxy-substituted 1-carbacephalosporins as intermediates for antibiotics
EP0266896B1 (de) * 1986-10-03 1992-08-05 Eli Lilly And Company 7-[(Meta-substituiert)-phenylglycin]-1-carba-1-dethia-cephalosporine
EP0299728A3 (de) * 1987-07-17 1989-08-23 Eli Lilly And Company Karbonylierungsverfahren für beta-Laktam-Antibiotika
US4782144A (en) * 1987-09-14 1988-11-01 Eli Lilly And Company 1-carba(dethia)-3-hydroxy-3-cephem ester crystalline and crystalline solvate thereof
US4885291A (en) * 1988-01-14 1989-12-05 Eli Lilly And Company 1-carba(dethia)-3-cephem derivatives
US5019571A (en) * 1988-01-25 1991-05-28 Eli Lilly And Company 1-carbacephalosporin antibiotics
US4855418A (en) * 1988-03-23 1989-08-08 Eli Lilly And Company Process for production of ceophalosporins
US4820832A (en) * 1988-03-23 1989-04-11 Eli Lilly And Company Process for preparing 3-unsubstituted cephalosporins and 1-carba(dethia)cephalosporins
US5191075A (en) * 1988-10-19 1993-03-02 Pfizer Inc Process for the preparation of penems
US4895940A (en) * 1988-10-19 1990-01-23 Pfizer Inc. Process for the preparation of penems
US4992543A (en) * 1988-10-19 1991-02-12 Pfizer Inc. Penem derivatives
US5159073A (en) * 1990-09-13 1992-10-27 Eli Lilly And Company Intermediates to 1-carbacephalosporins and process for preparation thereof
US5225553A (en) * 1990-09-13 1993-07-06 Eli Lilly And Company Intermediates to 1-carbacephalosporins and process for preparation thereof
US5169843A (en) * 1990-10-22 1992-12-08 Bristol-Myers Squibb Company Antibiotic C-3 cyclobutenedione substituted (1-carba) cephalosporin compounds, cmpositions, and methods of use thereof
US5206360A (en) * 1990-10-22 1993-04-27 Bristol-Myers Squibb Company Intermediates for cyclobutenedione substituted (1-carba)cephalosporin compounds
US5106842A (en) * 1990-10-22 1992-04-21 Bristol-Myers Squibb Co. Antibiotic c-3 cyclobutenedione substituted (1-carba)cephalosporin compounds, compositions, and methods of use thereof
US5099015A (en) * 1991-01-10 1992-03-24 Eli Lilly And Company Trifluoromethyl 1-carba(1-dethia)cephems
US5084447A (en) * 1991-04-25 1992-01-28 Eli Lilly And Company C-3 phosphine oxide substituted carbacephalosporins
WO1997030707A1 (en) 1996-02-23 1997-08-28 Eli Lilly And Company NON-PEPTIDYL VASOPRESSIN V1a ANTAGONISTS
CN107556212B (zh) * 2017-09-14 2020-03-24 台州昌霖化工科技有限公司 一种制备2-重氮乙酰乙酸对硝基苄酯的方法
CN112500361B (zh) * 2020-12-27 2023-05-12 甘肃瀚聚药业有限公司 一种(s)-4-苯基-2-恶唑烷酮的制备方法

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4226866A (en) * 1972-11-06 1980-10-07 Merck & Co., Inc. Novel antibiotic analogues of cephalosporins
US3925372A (en) * 1973-02-23 1975-12-09 Lilly Co Eli Alpha-aminoacyl-3-halo cephalosporins
US4275207A (en) * 1978-08-14 1981-06-23 Merck & Co., Inc. Process for preparing 7-(1-hydroxyethyl)-3-(2-aminoethylthio)-1-carbadethiaceph-3-em-3-carboxylic acid and intermediate therefor
JPS6058920B2 (ja) * 1978-12-26 1985-12-23 協和醗酵工業株式会社 セフアロスポリン類縁体
NO155548C (no) * 1979-02-10 1987-04-15 Kyowa Hakko Kogyo Kk Fremgangsmaate til fremstilling av optisk aktive cefalosporin-analoger.
JPS60174787A (ja) * 1984-02-21 1985-09-09 Kyowa Hakko Kogyo Co Ltd ３位置換カルバセフエム化合物
US4665171A (en) * 1985-07-17 1987-05-12 Harvard University Process and intermediates for β-lactam antibiotics
IE862850L (en) * 1985-11-21 1987-05-21 Inst Animal Health Ltd Intermediates for the preparation of beta-lactam antibiotics
JPH0791291B2 (ja) * 1985-12-30 1995-10-04 イ−ライ・リリ−・アンド・カンパニ− １−カルバセフアロスポリン抗生物質

Also Published As

Publication number Publication date
JPH07300475A (ja) 1995-11-14
GR861858B (en) 1986-11-18
ES2000589A6 (es) 1988-03-01
SU1547709A3 (ru) 1990-02-28
AU586694B2 (en) 1989-07-20
AU6014986A (en) 1987-02-05
JPS6259277A (ja) 1987-03-14
SG78091G (en) 1991-11-15
IL79421A (en) 1991-06-10
CN86105247A (zh) 1987-02-04
HUT41407A (en) 1987-04-28
IE861901L (en) 1987-02-02
IE58998B1 (en) 1993-12-15
CN1015103B (zh) 1991-12-18
KR900001883B1 (ko) 1990-03-26
CA1305964C (en) 1992-08-04
ZA865275B (en) 1988-02-24
EP0211540A1 (de) 1987-02-25
JPH0762016B2 (ja) 1995-07-05
EP0211540B1 (de) 1990-05-16
PT82990A (en) 1986-08-01
DK335786A (da) 1987-02-03
JP2529544B2 (ja) 1996-08-28
DE3671225D1 (de) 1990-06-21
CA1262356A (en) 1989-10-17
PT82990B (pt) 1989-01-30
DK335786D0 (da) 1986-07-15
KR870002123A (ko) 1987-03-30
HU201932B (en) 1991-01-28
NZ216872A (en) 1989-10-27
US4673737A (en) 1987-06-16
ATE52779T1 (de) 1990-06-15
PH22722A (en) 1988-11-28

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Legal Events

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PC Patent ceased (i.e. patent has lapsed due to the failure to pay the renewal fee)