FI96686B - Förfarande för framställning av farmakologiskt aktiva bensofusionerad-N-haltiga heterocykelderivat - Google Patents

Förfarande för framställning av farmakologiskt aktiva bensofusionerad-N-haltiga heterocykelderivat Download PDF

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FI96686B
FI96686B FI900553A FI900553A FI96686B FI 96686 B FI96686 B FI 96686B FI 900553 A FI900553 A FI 900553A FI 900553 A FI900553 A FI 900553A FI 96686 B FI96686 B FI 96686B
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methyl
azabicyclo
oct
compound
endo
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FI900553A
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Finnish (fi)
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FI96686C (sv
FI900553A0 (sv
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Arturo Donetti
Marco Turconi
Rosamaria Micheletti
Giovanni Battista Schiavi
Henri Nico Doods
Angelo Sagrada
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Boehringer Ingelheim Italia
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/02—1,2-Thiazines; Hydrogenated 1,2-thiazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • 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
    • 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
    • C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D401/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
    • C07D451/06—Oxygen atoms
    • C07D451/12—Oxygen atoms acylated by aromatic or heteroaromatic carboxylic acids, e.g. cocaine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/14—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing 9-azabicyclo [3.3.1] nonane ring systems, e.g. granatane, 2-aza-adamantane; Cyclic acetals thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • 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
    • C07D471/08—Bridged systems
    • 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
    • C07D487/08—Bridged systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Endocrinology (AREA)
  • Pulmonology (AREA)
  • Reproductive Health (AREA)
  • Urology & Nephrology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Photoreceptors In Electrophotography (AREA)
  • Indole Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Hydrogenated Pyridines (AREA)

Claims (6)

1. Förfarande för framställning av farmakologiskt aktiva bensofusionerad-N-haltiga heterocykelderivat med den allmänna 5 formeln (I) R ^ I ,νγ\
10 I 1/¾ (I) \c- X - Y II o 15 där R är H- eller ^.4 alkyl; R! och R2 är H, halogen, Cx_4 alkyl, alkoxi, hydroxi, cyano, karbamoyl; R3 är H, C^-4 alkyl, fenyl eller den är inte närvarande;
20 O / A är CO, C = S eller S ; \ O B är kväve, dä grupp R3 inte är närvarande och D-B-bindning är en enkel bindning, eller den är koi; /··. 25 D är CO, CH2-CH2, CH - R4, dä B-D-bindning är en enkel bind- • · ning, eller D är C-R, dä D-B-bindning är en dubbelbindning, där # R4 är H, Cx_4 alkyl, fenyl, hydroxi; I · 9 X är syre, N-R eller den är inte närvarande; . Y är en av följande basiska grupp: t : : ... 30 * · · • · · « 1 « I « « • I i' : « 1 t * * * :;·: 35 * ... . * 57 96686 -(CH2>„-< a) ^Rv 5 10 'Pk I ich2)0 15 (chj < β c) W R6 20 där n är 2 eller 3; p är 0 eller 1 samtidigt eller inte; q är : ' ' 0, 2 eller 3; Rg och R7 är oberoende av varandra H, C-j^ alkyl, : bensyl tai, Rg kan vara -C = N - R, där R8 är H, 1 1 .-. 25 R8 Ml t**·. eller amino och deras alia optiska isomerer, tautomerera former Ml och blandningar och deras syraadditionssalter, innersalter eller kvaternära derivat, kännetecknat därav, att a) en förening med den allmänna formeln (II) • ♦ « « * · _ _ ·.. 30 t · · • · · ♦ R Kj I . 3s *>4- ll i/R= (II) 58 96686 där R, R1# R2, R3, A, B och D avser det samma som ovan, som pä förhand är aktiverad med ett aktiveringsmedel tili ett reaktivt derivat med den allmänna formeln (IV) 5 R ^ 1 Ri--I l/R) „© (IV) ^ Ä /B' rs M 10 0 där M är en metallatom vald bland litium, natrium eller kalium, omsätts med en förening med formeln (III) 15 O Q - C - X - Y (I11^ 20 där X och Y avser det samma som ovan och Q är en avgäende ’ grupp, i ett aprotiskt losningsmedel vid en temperatur mellan - 50°C och rumstemperatur, .***: 25 b) dä B är koi och X är syre eller N - R, omsätts en förening j**'. med formeln (V) » « · • · · % 30 Ri— I l/R, (v) ks, JK. Λ ,. D 'Nt-Q Il : . . 0 ,: 35 59 96686 där R, R1, R2, R3, A och D avser det samma som ovan och Q är hydroxyl eller ovan definierad, med en förening med formeln (VI) 5 H - X - Y (VI) där X och Y avser det samma som ovan eller 10 c) dä B är kväve, R är väte och gruppen R3 inte är närvarande, en förening med den allmänna formeln (VII) 15 _ ' I (VII) Ri Γ" I - nh-c-x-y II o 20 där Rlf R2, D, X och Y avser det samma som ovan, omsätts med en :' ' 1 förening med den allmänna formeln (VII)
25 O *...· Il Γ"! Q, - C - Q, <VIII) t«· 1 2 i»< t : : « • · » • « · 30 där Qn och Q2/ som sinsemellan är identiska eller olika, är • » · f « * *. avgäende grupper, i ett aprotiskt lösningsmedel och eventuell i , närvaro av en syraacceptor vid en temperatur mellan 20°C och 100°C. ,·. : 35 2. Förfarande enligt patentkravet 1, kännetecknat därav, att den framställda föreningen är: 60 96686 1.4- dihydro-2(H)-2-oxo-3-kinazolinkarboxylsyra-(endo-8-metyl-8-azabicyklo[3.2.1]okt-3-yl), ester N-(endo-8-metyl-8-azabicyklo[3.2.1]okt-3-yl)-1,4-dihydro-2(H)-2-oxo-kinazolin-3-karboxamid 5 7-klor-l,4-dihydro-2(H)-2-oxo-3-kinazolinkarboxylsyra-(endo-8-metyl-8-azabicyklo[3.2.1]okt-3-yl), ester 1.4- dihydro-6-flour-2(H)-2-oxo-3-kinazolinkarboxylsyra-(endo-8-metyl-8-azabicyklo[3.2.1]okt-3-yl), ester 1.4- dihydro-8-hydroxi-2(H)-2-oxo-3-kinazolinkarboxylsyra-(endo-10 8-metyl-8-azabicyklo[3.2.1]okt-3-yl), ester ja deras fysiologiskt godtagbara syraadditionssalter. «*· • · • · » · · ·* « • · • i« 14» t i : i « • · · « · « • · · »I» • · · • · · « 0 I *
FI900553A 1989-02-06 1990-02-05 Förfarande för framställning av farmakologiskt aktiva bensofusionerad-N-haltiga heterocykelderivat FI96686C (sv)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT1931689 1989-02-06
IT8919316A IT1228293B (it) 1989-02-06 1989-02-06 Benzoderivati di composti eterociclici contenenti azoto.

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FI900553A0 FI900553A0 (sv) 1990-02-05
FI96686B true FI96686B (sv) 1996-04-30
FI96686C FI96686C (sv) 1996-08-12

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US (1) US5106851A (sv)
EP (1) EP0382687B1 (sv)
JP (1) JPH03197462A (sv)
KR (1) KR900012919A (sv)
AT (1) ATE132140T1 (sv)
AU (1) AU623733B2 (sv)
CA (1) CA2009300A1 (sv)
CZ (1) CZ277886B6 (sv)
DE (1) DE69024381T2 (sv)
DK (1) DK0382687T3 (sv)
ES (1) ES2081966T3 (sv)
FI (1) FI96686C (sv)
GR (1) GR3018549T3 (sv)
HU (2) HUT54118A (sv)
IL (1) IL93257A (sv)
IT (1) IT1228293B (sv)
MX (1) MX19368A (sv)
NO (1) NO173500C (sv)
PL (1) PL162682B1 (sv)
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EP0382687A3 (en) 1991-12-04
CA2009300A1 (en) 1990-08-06
FI96686C (sv) 1996-08-12
ZA90825B (en) 1991-10-30
EP0382687B1 (en) 1995-12-27
IT8919316A0 (it) 1989-02-06
FI900553A0 (sv) 1990-02-05
IL93257A (en) 1994-07-31
YU21590A (sh) 1993-05-28
ATE132140T1 (de) 1996-01-15
HU900671D0 (en) 1990-04-28
HUT54118A (en) 1991-01-28
PL283642A1 (en) 1991-02-11
NO173500B (no) 1993-09-13
NO900542L (no) 1990-08-07
RU2040524C1 (ru) 1995-07-25
NO173500C (no) 1993-12-22
HU210348A9 (en) 1995-03-28
IT1228293B (it) 1991-06-07
PL162682B1 (pl) 1993-12-31
DE69024381T2 (de) 1996-05-15
DE69024381D1 (de) 1996-02-08
AU4908690A (en) 1990-10-25
MX19368A (es) 1993-09-01
GR3018549T3 (en) 1996-03-31
JPH03197462A (ja) 1991-08-28
NO900542D0 (no) 1990-02-05
CZ33590A3 (en) 1993-02-17
IL93257A0 (en) 1990-11-29
PT93066A (pt) 1990-08-31
AU623733B2 (en) 1992-05-21
CZ277886B6 (en) 1993-06-16
PT93066B (pt) 1997-01-31
KR900012919A (ko) 1990-09-03
ES2081966T3 (es) 1996-03-16
DK0382687T3 (da) 1996-02-05
US5106851A (en) 1992-04-21
EP0382687A2 (en) 1990-08-16

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