FI96947B - Förfarande för framställning av terapeutiskt aktiva N1-(1,2-cis-2-halogencyklopropyl)substituerade pyridonkarboxylsyraderivat - Google Patents

Förfarande för framställning av terapeutiskt aktiva N1-(1,2-cis-2-halogencyklopropyl)substituerade pyridonkarboxylsyraderivat Download PDF

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Publication number
FI96947B
FI96947B FI891980A FI891980A FI96947B FI 96947 B FI96947 B FI 96947B FI 891980 A FI891980 A FI 891980A FI 891980 A FI891980 A FI 891980A FI 96947 B FI96947 B FI 96947B
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FI
Finland
Prior art keywords
cis
carboxylic acid
amino
oxo
fluoro
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FI891980A
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English (en)
Finnish (fi)
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FI96947C (sv
FI891980A (sv
FI891980A0 (sv
Inventor
Isao Hayakawa
Youichi Kimura
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Daiichi Seiyaku Co
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.)
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Publication date
Application filed by Daiichi Seiyaku Co filed Critical Daiichi Seiyaku Co
Publication of FI891980A0 publication Critical patent/FI891980A0/sv
Publication of FI891980A publication Critical patent/FI891980A/sv
Application granted granted Critical
Publication of FI96947B publication Critical patent/FI96947B/sv
Publication of FI96947C publication Critical patent/FI96947C/sv

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
    • 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
    • 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
    • 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

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  • 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyridine Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Claims (2)

1. Förfarande för framställning av terapeutiskt aktiva N., - (1,2-cis-2-halogencyklopropyl) substituerade 5 pyridonkarboxylsyraderivat med formeln (I): χά~ - väri R1 är en aminogrupp eller väteatom; A är en kväve-atom eller C-X3, väri X3 är en halogenatom, en alkyl-15 grupp med 1-6 kolatomer eller en alkoxigrupp med 1 -6 kolatomer och R2 är en cyklisk aminogrupp med formeln ·· ·>ϊί- . H R11 väri R6 och R11, som kan vara sana eller olika, beteck-nar en alkylgrupp med 1-6 kolatomer eller en väteato-25 m; och R12 och R13 är förbundna med varandra sä, att de t bildar en polymetylenkedja med 2-5 kolatomer; och farmaceutiskt godtagbara salter därav, eventuellt i en stereoisomeriskt ren form, kännetecknat av att en 7-halogen-l-(l,2-cis-2-halogencyklopropyl)pyri-30 donkarboxylsyra med formeln Λ R1 0 xo, t : , Uii MB 1:1 i M 77 96947 väri R1 och A är ovan definierade och X är en halogen-atom, eller en ester eller ett difluorborderivat därav omsätts med en cyklisk aminförening R2-H, som kan vara skyddad med en sedvanlig skyddsgrupp och väri R2 är som 5 ovan definierats, och därefter avlägsnas skyddsgruppen, om sä önskas, medelst ett sedvanligt förfarande och, om sä önskas, avlägsnas estergruppen eller difluorborgrup-pen under sura eller basiska förhällanden.
2. Förfarande enligt patentkrav 1, k ä n n e -10 tecknat av att man framställer 7-[3-(S)-araino- l-pyrrolidinyl]-6-fluor-l-(l,2-cis-2-fluorcyklopropyl)- 4-oxo-1,4-dihydrokinolin-3-karboxylsyra, 7-[3-(S)-ami-no-l-pyrrolidinyl] -8-klor-6-f luor-1- (1,2-cis-f luorcyk-lopropyl)4-oxo-l,4-dihydrokinolin-3-karboxylsyra, 7-15 [7-amino-5-azaspiro[2.4)heptan-5-yl]-8-klor-6-fluor- 1- (1,2-cis-2-f luorcyklopropyl) -4-oxo-l,4-dihydrokino-lin-3-karboxylsyra, 5-amino-7-[3-(S)-amino-l-pyrrolidi-nyl]-6,8-difluor-1-(1,2-cis-2-fluorcyklopropyl)-4-oxo- 1,4-dihydrokinolin-3-karboxylsyra, 7-[4-(S)-amino-2- 20 (S) -raetyl-l-pyrrolidinyl]-6-fluor-1-(1,2-cis-2-f luor- cy k 1 opr opy 1) - 4 -oxo-1,4 -dihydr o-1,8 -naf ty r idin- 3 -karbox-ylsyra, 7-[3-(R)-[1-(S)-aminoetyl]-l-pyrrolidinyl]-8-klor-6-f luor-1- (1,2-cis-2-f luorcyklopropyl) -4-oxo-l, 4-dihydrokinolin-3-karboxylsyra, 7-[3-amino-4-metyl-l- 25 pyrrolidinyl]-6-fluor-l-(l,2-cis-2-fluorcyklopropyl)- 8-metoxi-4-oxo-l,4-dihydrokinolin-3-karboxylsyra, 7-[4 —(S) -amino-2-(S) -metyl-1-pyrrolidinyl] -6-f luor-1-(1,2-cis-2-f luorcyklopropyl) -8-metyl-4-oxo-l, 4-dihydro-kinolin-3-karboxylsyra eller 5-amino-7-[7-amino-5-aza-30 spiro[2.4) heptan-5-y 1 ] -6,8-dif luor-1- (1,2-cis-2-f luor cyklopropyl) -4-oxo-l,4-dihydrokinolin-3-karboxylsyra ’ eller ett sait som bildats av nägot av dessa.
FI891980A 1988-04-27 1989-04-26 Förfarande för framställning av terapeutiskt aktiva N1-(1,2-cis-2-halogencyklopropyl)substituerade pyridonkarboxylsyraderivat FI96947C (sv)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP10462588 1988-04-27
JP10462588 1988-04-27
JP29698488 1988-11-24
JP29698488 1988-11-24

Publications (4)

Publication Number Publication Date
FI891980A0 FI891980A0 (sv) 1989-04-26
FI891980A FI891980A (sv) 1989-10-28
FI96947B true FI96947B (sv) 1996-06-14
FI96947C FI96947C (sv) 1996-09-25

Family

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Application Number Title Priority Date Filing Date
FI891980A FI96947C (sv) 1988-04-27 1989-04-26 Förfarande för framställning av terapeutiskt aktiva N1-(1,2-cis-2-halogencyklopropyl)substituerade pyridonkarboxylsyraderivat

Country Status (26)

Country Link
US (4) US5587386A (sv)
EP (1) EP0341493B1 (sv)
JP (5) JP2714597B2 (sv)
KR (1) KR0184614B1 (sv)
CN (1) CN1033751C (sv)
AT (1) ATE182145T1 (sv)
AU (1) AU625414B2 (sv)
BG (1) BG61122B2 (sv)
CA (1) CA1340801C (sv)
DE (1) DE68929030T2 (sv)
DK (1) DK175467B1 (sv)
ES (1) ES2135372T3 (sv)
FI (1) FI96947C (sv)
GR (1) GR3031365T3 (sv)
HK (1) HK1002108A1 (sv)
HU (1) HU211136A9 (sv)
IL (1) IL90062A (sv)
LV (1) LV10092B (sv)
MY (1) MY105136A (sv)
NO (1) NO175939C (sv)
NZ (1) NZ228893A (sv)
PT (1) PT90377B (sv)
RU (1) RU2075475C1 (sv)
SG (1) SG48036A1 (sv)
UA (1) UA29378C2 (sv)
YU (1) YU48432B (sv)

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TWI386401B (zh) * 2006-03-27 2013-02-21 Daiichi Seiyaku Co 醫藥用水合物
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JP5414395B2 (ja) 2008-07-11 2014-02-12 住友化学株式会社 （１ｓ，２ｒ）−２−クロロ−２−フルオロシクロプロパンカルボン酸の製造方法
FR2961207B1 (fr) * 2010-06-09 2013-01-18 Oreal Utilisation d'un derive de 4- carboxy 2-pyrrolidinone comme solvant dans les compositions cosmetiques ; compositions cosmetiques les contenant ; nouveaux composes
CN103467448B (zh) * 2013-09-18 2015-04-15 浙江司太立制药股份有限公司 7-(3-氨基-4-烷氧亚胺基-1-哌啶基)-1-[(1r,2s)-2-氟环丙基]喹诺酮羧酸类化合物及其制备方法
EP2957561A1 (en) * 2014-06-18 2015-12-23 Université Paris 6 Pierre et Marie Curie UPMC Novel fluoroquinolones and use thereof to treat bacterial infections
CN105330590B (zh) * 2015-10-15 2018-09-25 广州市朗启医药科技有限责任公司 西他沙星五元环侧链中间体的制备方法
CN109912504B (zh) * 2019-04-04 2020-11-10 山东省联合农药工业有限公司 一种喹啉羧酸类化合物及其制备方法与用途

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Also Published As

Publication number Publication date
BG61122B2 (bg) 1996-11-29
AU625414B2 (en) 1992-07-09
EP0341493A3 (en) 1990-12-19
ATE182145T1 (de) 1999-07-15
HU211136A9 (en) 1995-10-30
JPH1067779A (ja) 1998-03-10
UA29378C2 (uk) 2000-11-15
EP0341493B1 (en) 1999-07-14
SG48036A1 (en) 1998-04-17
US5587386A (en) 1996-12-24
JPH02231475A (ja) 1990-09-13
DK205789A (da) 1989-10-28
LV10092B (en) 1995-02-20
PT90377B (pt) 1994-09-30
EP0341493A2 (en) 1989-11-15
AU3370289A (en) 1989-11-02
DE68929030T2 (de) 2000-03-23
KR900016205A (ko) 1990-11-12
JP2714597B2 (ja) 1998-02-16
MY105136A (en) 1994-08-30
NO175939B (no) 1994-09-26
NZ228893A (en) 1990-06-26
CN1037507A (zh) 1989-11-29
US6031102A (en) 2000-02-29
NO891698D0 (no) 1989-04-25
DE68929030D1 (de) 1999-08-19
YU48432B (sh) 1998-07-10
FI96947C (sv) 1996-09-25
FI891980A (sv) 1989-10-28
CA1340801C (en) 1999-10-26
JP2917010B2 (ja) 1999-07-12
CN1033751C (zh) 1997-01-08
USRE41149E1 (en) 2010-02-23
NO175939C (no) 1995-01-04
RU2075475C1 (ru) 1997-03-20
IL90062A0 (en) 1989-12-15
JPH07300416A (ja) 1995-11-14
PT90377A (pt) 1989-11-10
NO891698L (no) 1989-10-30
FI891980A0 (sv) 1989-04-26
US5767127A (en) 1998-06-16
JPH11124367A (ja) 1999-05-11
IL90062A (en) 1994-10-07
HK1002108A1 (en) 1998-07-31
JPH11124380A (ja) 1999-05-11
YU87589A (en) 1990-12-31
GR3031365T3 (en) 2000-01-31
JP2903292B2 (ja) 1999-06-07
KR0184614B1 (ko) 1999-05-01
DK205789D0 (da) 1989-04-27
ES2135372T3 (es) 1999-11-01
DK175467B1 (da) 2004-11-01

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