FI106962B - Förfarande för framställning av (1R, 5S, 6S)-2-[1-(1,3-tiazolin-2-yl)azetidin-3-yl]-tio-6-[(R)-1-hydroxietyl]-1-metylkarbapen-2-em-3-karboxylsyraderivat - Google Patents

Förfarande för framställning av (1R, 5S, 6S)-2-[1-(1,3-tiazolin-2-yl)azetidin-3-yl]-tio-6-[(R)-1-hydroxietyl]-1-metylkarbapen-2-em-3-karboxylsyraderivat Download PDF

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Publication number
FI106962B
FI106962B FI943164A FI943164A FI106962B FI 106962 B FI106962 B FI 106962B FI 943164 A FI943164 A FI 943164A FI 943164 A FI943164 A FI 943164A FI 106962 B FI106962 B FI 106962B
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Finland
Prior art keywords
compound
formula
group
compounds
azetidin
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FI943164A
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English (en)
Finnish (fi)
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FI943164A0 (sv
FI943164L (sv
Inventor
Takao Abe
Satoshi Tamai
Chisato Sato
Ado Mihira
Takeshi Isoda
Toshio Kumagai
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Wyeth Lederle Japan Ltd
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Application filed by Wyeth Lederle Japan Ltd filed Critical Wyeth Lederle Japan Ltd
Publication of FI943164A0 publication Critical patent/FI943164A0/sv
Publication of FI943164L publication Critical patent/FI943164L/sv
Application granted granted Critical
Publication of FI106962B publication Critical patent/FI106962B/sv

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
    • C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and 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
    • C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and 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 hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
    • C07D477/16—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and 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 hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hetero atoms or carbon atoms 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 3
    • C07D477/20—Sulfur atoms
    • 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
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Communicable Diseases (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Claims (6)

1. H I 3 /\ .ö— CH AiVA/S—<. n-^, (ll) 3 .TT II n-1 30 Λ \ o C00H eller dess farmaceutiskt godtagbara sait.
1. Förfarande för framställning av ett terapeu-5 tiskt användbart (1R, 5S, 6S)-2-[l-(1,3-tiazolin-2-yl)azeti-din-3-yl]-tio-6-[ (R) -l-hydroxietyl]-l^metylkar-bapen-2-em- 3-karboxylsyraderivat med formeln: HT H H f3 sn
10. AiJ>vs‘V'N“^ (,) % Il v n—L A- N-\ XR o Y väri R är väte; en Ci-14-alkylgrupp som är substi-15 tuerad med en Ci~4-alkoxi-Ci-4alkoxigrupp; eller en grupp -CONR2R3 (R2 och R3 är oberoende av varandra Ci-4-alkyl) Y är karboxi, -COO, p-nitrobenzyloxikarbonyl, Ci-6-alkoxi-CO-Ci-4-alkoxi-CO eller C3-7-cykloakyl-0-C0-0-Ci-4-alkoxi-C0-, eller för framställning av dess farmaceutiskt godtagbara 20 sait, kännetecknat av att en förening med formeln: H? H H fi 0Ra CH3 ι"+ιΓ /“N—^ : „ 0 COOR’ 25 (VII!) väri Ra är en acylgrupp och R' är en karboxyls-kyddsgrupp, fas att reagera med förening med formeln: . · 30 οχ) A väri R har samma betydelse som ovan, varvid er-35 hälls en förening med formeln: 60 106962 , 0 C00R' 5 (X) väri R och R' har samma betydelse som ovan, däref-ter utsätts den erhällna föreningen enligt formel (X) för avlägsnande av karboxylskyddsgruppen, varvid erhälls en 10 förening med formeln: Λϋ^-0-<Π C00H 15 (VI f) väri R har samma betydelse som ovan, eller farmaceutiskt godtagbart sait, därefter utsätts vid behov den erhällna föreningen engligt formel 20 (VII) för förestring av karboxigruppen, varvid föreningen som visats med formel (I) erhälls.
2. Förfarande enligt patentkrav 1, kanne-tecknat av att föreningen enligt formel (1R,5S,6S)~ 2—[1 — (1,3-tiazolin-2-yl) azetidin-3-yl]-tio-6-[ (R) -1-hyd- ’ 25 roxietyl]-l-metylkarbapen-2-em-3-karboxylsyra med följande formel:
3. V-V0CH3 (f COOK ^ eller dess farmaceutiskt godtagbara salt. 35 62 106962
3. Förfarande enligt patentkrav 1, kanne- 35 tecknat av att föreningen enligt formel (I) är 1-[ (cyklohexyloxi) karbonyloxi]-etyl- (1R, 5S, 6S) —2—[1— (1,3- 61 106962 tiazolin-2-yl) azetidin-3-yl]tio-6-[ (R) -l-hydroxietyl]-l-metylkarbapen-2-em-3-karboxylat, med följande formel: CH3 T] if V N_J (IV) C00CH-0C0- I II N—/ ch3 0 10 eller dess farmaceutiskt godtagbara salt.
4. Förfarande enligt patentkrav 1, kanne-tecknat av att föreningen enligt formel (I) är pi-valoyloximetyl-(1R,5S, 6S) —2—[1 — (1,3-tiazolin-2-yl)azeti- 15 din-3-y]tio-6-[ (R) -l-hydroxietyl]-l-metylkarbapen-2-em-3- karboxylat med formeln «/Τ'·! {j ^ N—J
20. J- N—\
0 C0QCH20C0-t-But eller dess farmaceutiskt godtagbara salt.
5. Förfarande enligt patentkrav 1, k ä n n e - : 25tecknat av att föreningen enligt formel (I) är en (1R, 5S, 6S) -2-[l- ( (4R)metoxi-metyloximetyl-l, 3-tiazolin-2-yl) azetidin-3-yl]tio-6-[ (R) -l-hydroxietyl]-l-metylkarbapen- 2-em-3-karboxylsyra med formeln . · 30 " H ^ sn
6. Förfarande enligt patentkrav 1, k ä n n e-tecknat av att föreningen enligt formel (I) är en (1R, 5S, 6S) — 2 — [1 — ( (4R) -dimetylaminokarbonyl-1,3-tiazolin-2-yl) azetidin-3-yl]tio-6-[ (R) -l-hydroxietyl]-l-metylkarbapen-5 2-em-3-karboxylsyra med formeln ΝΛ<*3 CT COQH CHn 10 0 eller dess farmaceutiskt godtagbara sait.
FI943164A 1993-07-01 1994-07-01 Förfarande för framställning av (1R, 5S, 6S)-2-[1-(1,3-tiazolin-2-yl)azetidin-3-yl]-tio-6-[(R)-1-hydroxietyl]-1-metylkarbapen-2-em-3-karboxylsyraderivat FI106962B (sv)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP21330693 1993-07-01
JP21330693 1993-07-01
JP7932094 1994-03-28
JP7932094 1994-03-28
JP12204694 1994-05-12
JP12204694 1994-05-12

Publications (3)

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FI943164A0 FI943164A0 (sv) 1994-07-01
FI943164L FI943164L (sv) 1995-01-02
FI106962B true FI106962B (sv) 2001-05-15

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FI943164A FI106962B (sv) 1993-07-01 1994-07-01 Förfarande för framställning av (1R, 5S, 6S)-2-[1-(1,3-tiazolin-2-yl)azetidin-3-yl]-tio-6-[(R)-1-hydroxietyl]-1-metylkarbapen-2-em-3-karboxylsyraderivat

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US (2) US5534510A (sv)
EP (2) EP0924210B1 (sv)
JP (1) JP2666118B2 (sv)
KR (1) KR100331293B1 (sv)
AT (2) ATE212636T1 (sv)
AU (1) AU682510B2 (sv)
CA (1) CA2127193C (sv)
DE (2) DE69433955T2 (sv)
DK (2) DK0632039T3 (sv)
ES (2) ES2222630T3 (sv)
FI (1) FI106962B (sv)
HU (1) HU220609B1 (sv)
IL (1) IL110161A (sv)
NO (2) NO306780B1 (sv)
PT (2) PT632039E (sv)
TW (1) TW254943B (sv)

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CN103059026A (zh) * 2011-10-20 2013-04-24 北京康健源科技有限公司 一种替比培南匹夫酯的制备方法
CN102584812B (zh) * 2011-11-18 2014-03-12 深圳万乐药业有限公司 一种泰比培南酯杂质的制备方法
CN102503940B (zh) * 2011-11-22 2013-12-25 深圳万乐药业有限公司 制备泰比培南酯开环杂质的方法
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JP2666118B2 (ja) 1997-10-22
IL110161A (en) 1998-09-24
DK0632039T3 (da) 2002-05-13
HUT68057A (en) 1995-05-29
KR950003292A (ko) 1995-02-16
JPH0853453A (ja) 1996-02-27
HU9401957D0 (en) 1994-09-28
DK0924210T3 (da) 2004-12-13
US5534510A (en) 1996-07-09
EP0924210A1 (en) 1999-06-23
AU682510B2 (en) 1997-10-09
CA2127193C (en) 2005-04-12
ES2222630T3 (es) 2005-02-01
DE69429742T2 (de) 2002-06-06
ATE212636T1 (de) 2002-02-15
AU6598794A (en) 1995-01-12
EP0632039B1 (en) 2002-01-30
NO306780B1 (no) 1999-12-20
US5679790A (en) 1997-10-21
IL110161A0 (en) 1994-10-07
CA2127193A1 (en) 1995-01-02
DE69429742D1 (de) 2002-03-14
HU220609B1 (hu) 2002-03-28
NO942483L (no) 1995-01-02
EP0924210B1 (en) 2004-08-18
PT632039E (pt) 2002-06-28
DE69433955D1 (de) 2004-09-23
ES2170080T3 (es) 2002-08-01
NO307379B1 (no) 2000-03-27
EP0632039A1 (en) 1995-01-04
NO942483D0 (no) 1994-06-30
FI943164A0 (sv) 1994-07-01
PT924210E (pt) 2004-12-31
ATE273975T1 (de) 2004-09-15
DE69433955T2 (de) 2005-09-08
FI943164L (sv) 1995-01-02
KR100331293B1 (ko) 2002-10-25
NO991019L (no) 1995-01-02
TW254943B (sv) 1995-08-21
NO991019D0 (no) 1999-03-02

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