FI86721B - Foerfarande foer framstaellning av terapeutiskt anvaendbara 1-cyklopropyl-1,4-dihydro-4-oxo-1,8-naftyridin-3-karboxylsyror. - Google Patents

Foerfarande foer framstaellning av terapeutiskt anvaendbara 1-cyklopropyl-1,4-dihydro-4-oxo-1,8-naftyridin-3-karboxylsyror. Download PDF

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Publication number
FI86721B
FI86721B FI860073A FI860073A FI86721B FI 86721 B FI86721 B FI 86721B FI 860073 A FI860073 A FI 860073A FI 860073 A FI860073 A FI 860073A FI 86721 B FI86721 B FI 86721B
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Finland
Prior art keywords
oxo
dihydro
naphthyridine
cyclopropyl
formula
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FI860073A
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English (en)
Finnish (fi)
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FI86721C (sv
FI860073A (fi
FI860073A0 (fi
Inventor
Karl Georg Metzger
Hans-Joachim Zeiler
Uwe Petersen
Klaus Grohe
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Bayer Ag
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Publication of FI860073A0 publication Critical patent/FI860073A0/fi
Publication of FI860073A publication Critical patent/FI860073A/fi
Priority to FI892675A priority Critical patent/FI892675A/fi
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Publication of FI86721C publication Critical patent/FI86721C/sv

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/72—Nitrogen atoms
    • C07D213/76—Nitrogen atoms to which a second hetero atom is attached
    • C07D213/77—Hydrazine radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • 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

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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)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Peptides Or Proteins (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)

Claims (8)

1. Förfarande för framställning av terapeutiskt användbaral-cyklopropyl-1,4-dihydro-4-oxo-l,8-naftyridin-5 3-karboxylsyror med formeln I λχτΥ“ R1-N (I) A 15 väri X betecknar halogen, R1 betecknar väte, en förgrenad eller oförgrenad alkylgrupp, vilken har 1-4 kolatomer och vilken eventuellt är subtituerad med en hydroxigrupp, 20 eller en oxoalkylgrupp med 2-4 kolatomer och R3 betecknar väte, metyl eller fenyl, förutsatt att, dä R1 är väte eller metyl, är R3 ej väte och X är ej fluor, och farmaceutiskt godtagbara syraadditionssalter därav, känneteck-n a t därav, att 25 a) för framställning av föreningar med formeln I, väri X, R1 och R3 betecknar samma som ovan, omsätts 1-cyk-lopropyl-7-halogen-l,4-dihydro-4-oxo-l,8-naftyridin-3-karboxylsyror med formeln II 30 -- COOH Xjl J Y N A väri X betecknar halogen och Y betecknar halogen, företrä- desvis klor eller fluor, med aminer med formeln III 34 86721
2. Förfarande enligt patentkravet 1, känne- 10 tecknat därav, att man framställer 1-cyklopropyl- 6-fluor-l, 4-dihydro-7-[4-( 2-oxopropyl) -1-piperazinyl] -4-oxo-1,8-naftyridin-3-karboxylsyra.
3. Förfarande enligt patentkravet 1, känne-tecknat därav, att man framställer 6-fluor-l-cyklo- 15 propyl-1,4-dihydro-4-oxo-7- [4- (3-oxobutyl) -1 -piperazinyl] - 1,8-naftyridin-3-karboxylsyra.
4. Förfarande enligt patentkravet 1, känne-tecknat därav, att man framställer 1-cyklopropyl- 6-fluor-7- [4— (2-hydroxietyl)-1-piperazinyl] -1,4-dihydro- 20 4-oxo-1,8-naftyridin-3-karboxylsyra.
5. Förfarande enligt patentkravet 1, känne-tecknat därav, att man framställer 6-klor-l-cyklo-propyl-1,4-dihydro-7-(4-metyl-l-piperazinyl)-4-oxo-l,8-naftyridin-3-karboxylsyra. 25
6. Förfarande enligt patentkravet 1, känne- tecknat därav, att man framställer 6-fluor-l-cyklo-propyl-1,4-dihydro-7-(3-metyl-l-piperazinyl)-4-oxo-l,8-naftyridin-3-karboxylsyra.
5 CH3-CO-CH=CH2 (VI) och Ifall önskvärt, överförs de erhällna före-nlngarna med formeln I tili salter eller estrar.
5 R-N H-H väri R1 och R3 betecknar sanuna som ovan, eventuellt i när-varo av syrabindande medel, eller 10 b) för framställning av föreningar med formeln I, väri R1 betecknar en förgrenad eller oförgrenad alkylgrupp, vilken har 1-4 kolatomer och vilken eventuellt är subti-tuerad med en hydroxigrupp, eller en oxoalkylgrupp med 2 -4 kolatomer och R3 betecknar väte, metyl eller fenyl, för-15 utsatt att, dä R1 är metyl, är R3 ej väte och X är ej fluor, omsätts 1-cyklopropyl-l,4-dihydro-4-oxo-7-(1-pipe-razinyl)-l,8-naftyridin-3-karboxylsyror med formeln IV 0 20. i C00I1 nl jl Γ ™ N—(IV) A 25 väri X och R3 betecknar samma som ovan, med föreningar med formeln v Rx-Z (V) 30 väri R1 betecknar samma som ovan och Z betecknar halogen, företrädesvis klor, brom eller jod, acyloxi, etoxi eller hydroxi, eventuellt i närvaro av syrabindande medel, eller c) för framställning av föreningar med formeln I, 35 väri R1 betecknar gruppen CH3-CO-CH2-CH2- och R3 betecknar väte, metyl eller fenyl, omsätts en förening med formeln IV, väri X och R3 betecknar sanuna som i punkten b), med metylvinylketonet med formeln VI 35 86721
7. Förfarande enligt patentkravet 1, känne- 30 tecknat därav, att man framställer 6-fluor-l-cyklo- propyl-7-(4-etyl-l-piperazinyl )-l, 4-dihydro-4-oxo-l, 8-naf-tyridin-3-karboxylsyra.
8. Förfarande enligt patentkravet 1, känne-tecknat därav, att man framställer 6-fluor-l-cyklo- 35 propyl-1,4-dihydro-4-oxo-7-(3-fenyl-l-piperazinyl)-1,8- naftyridin-3-karboxylsyra.
FI860073A 1985-01-10 1986-01-08 Förfarande för framställning av terapeutiskt användbara 1-cyklopropyl- 1,4-dihydro-4-oxo-1,8-naftyridin-3-karboxylsyror FI86721C (sv)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FI892675A FI892675A (fi) 1985-01-10 1989-06-01 2,6-dihalogenpyridin-3 -karboxylsyraderivat och deras framstaellning.

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE3500562 1985-01-10
DE3500562 1985-01-10
DE19853508816 DE3508816A1 (de) 1985-01-10 1985-03-13 6,7-disubstituierte 1-cyclopropyl-1,4-dihydro-4-oxo-1,8-naphtyridin-3-carbonsaeuren
DE3508816 1985-03-13

Publications (4)

Publication Number Publication Date
FI860073A0 FI860073A0 (fi) 1986-01-08
FI860073A FI860073A (fi) 1986-07-11
FI86721B true FI86721B (fi) 1992-06-30
FI86721C FI86721C (sv) 1992-10-12

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Application Number Title Priority Date Filing Date
FI860073A FI86721C (sv) 1985-01-10 1986-01-08 Förfarande för framställning av terapeutiskt användbara 1-cyklopropyl- 1,4-dihydro-4-oxo-1,8-naftyridin-3-karboxylsyror
FI892675A FI892675A (fi) 1985-01-10 1989-06-01 2,6-dihalogenpyridin-3 -karboxylsyraderivat och deras framstaellning.

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FI892675A FI892675A (fi) 1985-01-10 1989-06-01 2,6-dihalogenpyridin-3 -karboxylsyraderivat och deras framstaellning.

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US (1) US4840954A (sv)
EP (1) EP0187376B1 (sv)
JP (1) JPH0653741B2 (sv)
KR (1) KR910002645B1 (sv)
CN (1) CN1003236B (sv)
AT (1) ATE76076T1 (sv)
AU (3) AU574550B2 (sv)
CA (2) CA1339373C (sv)
DE (2) DE3508816A1 (sv)
DK (1) DK168439B1 (sv)
ES (5) ES8802520A1 (sv)
FI (2) FI86721C (sv)
GR (1) GR860031B (sv)
HU (1) HU193623B (sv)
IE (1) IE58412B1 (sv)
IL (2) IL77538A (sv)
NO (2) NO163331C (sv)
NZ (2) NZ229861A (sv)
PH (2) PH25055A (sv)
PL (2) PL148191B1 (sv)
PT (1) PT81810B (sv)

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KR910002645B1 (ko) 1991-04-27
NZ229861A (en) 1989-10-27
EP0187376B1 (de) 1992-05-13
DK9186D0 (da) 1986-01-09
ES8801919A1 (es) 1988-03-01
FI86721C (sv) 1992-10-12
EP0187376A2 (de) 1986-07-16
CN86100126A (zh) 1986-07-09
US4840954A (en) 1989-06-20
ES8800222A1 (es) 1987-10-16
ES557516A0 (es) 1987-10-16
CN1003236B (zh) 1989-02-08
NO860199L (no) 1986-07-11
AU1835988A (en) 1988-09-15
IE860062L (en) 1986-07-10
AU574550B2 (en) 1988-07-07
ES8802225A1 (es) 1988-04-16
DK9186A (da) 1986-07-11
ES550767A0 (es) 1988-06-16
PT81810B (pt) 1988-05-27
FI892675A0 (fi) 1989-06-01
CA1339373C (en) 1997-08-26
PL148759B1 (en) 1989-11-30
JPS61161284A (ja) 1986-07-21
NO163331B (no) 1990-01-29
NZ214746A (en) 1989-10-27
EP0187376A3 (en) 1988-05-04
AU5216486A (en) 1987-01-22
PH25055A (en) 1991-01-28
DE3508816A1 (de) 1986-07-10
HUT40126A (en) 1986-11-28
IE58412B1 (en) 1993-09-22
DE3586048D1 (en) 1992-06-17
ES557785A0 (es) 1988-04-16
ES557515A0 (es) 1988-02-16
PH24769A (en) 1990-10-01
GR860031B (en) 1986-04-29
NO163331C (no) 1990-05-09
KR860005818A (ko) 1986-08-13
FI892675A (fi) 1989-06-01
PT81810A (en) 1986-02-01
PL264565A1 (en) 1988-01-07
DK168439B1 (da) 1994-03-28
ATE76076T1 (de) 1992-05-15
ES8801796A1 (es) 1988-02-16
PL257419A1 (en) 1987-07-27
AU576449B2 (en) 1988-08-25
CA1320206C (en) 1993-07-13
AU7311887A (en) 1987-09-10
FI860073A (fi) 1986-07-11
ES557514A0 (es) 1988-03-01
IL77538A (en) 1992-05-25
ES8802520A1 (es) 1988-06-16
FI860073A0 (fi) 1986-01-08
JPH0653741B2 (ja) 1994-07-20
IL89168A0 (en) 1989-09-10
PL148191B1 (en) 1989-09-30
NO855134L (no) 1986-07-11
HU193623B (en) 1987-11-30

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