FI95031B - Förfarande för framställning av heterocykliska föreningar - Google Patents

Förfarande för framställning av heterocykliska föreningar Download PDF

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Publication number
FI95031B
FI95031B FI885917A FI885917A FI95031B FI 95031 B FI95031 B FI 95031B FI 885917 A FI885917 A FI 885917A FI 885917 A FI885917 A FI 885917A FI 95031 B FI95031 B FI 95031B
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Finland
Prior art keywords
amino
azabicyclo
carbonyl
octan
formula
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FI885917A
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English (en)
Finnish (fi)
Other versions
FI95031C (sv
FI885917A (sv
Inventor
Terence James Ward
Janet Christine White
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Wyeth John & Brother Ltd
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Priority claimed from GB878730193A external-priority patent/GB8730193D0/en
Priority claimed from GB888819728A external-priority patent/GB8819728D0/en
Application filed by Wyeth John & Brother Ltd filed Critical Wyeth John & Brother Ltd
Publication of FI885917A publication Critical patent/FI885917A/sv
Publication of FI95031B publication Critical patent/FI95031B/sv
Application granted granted Critical
Publication of FI95031C publication Critical patent/FI95031C/sv

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    • 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
    • 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
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/06—Antimigraine agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/20—Hypnotics; Sedatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/04—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • 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
    • C07D451/10—Oxygen atoms acylated by aliphatic or araliphatic carboxylic acids, e.g. atropine, scopolamine
    • 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
    • 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
    • C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
  • Otolaryngology (AREA)
  • Psychiatry (AREA)
  • Hospice & Palliative Care (AREA)
  • Anesthesiology (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Claims (10)

1. Förfarande för framställning av en terapeutiskt användbar heterocyklisk förening med den allmänna formeln 5 A-CO-NHCW-Y-B (I ) eller för framställning av ett farmaceutiskt godtagbart syraadditionssalt därav, i vilken formel 10 A betecknar en aromatisk radikal med formeln 15 (a) * (b) tai (c) där den fria valensen är ansluten tili fusionsringen i formel a), Rl betecknar väte eller en eller flera lika eller 20 olika substituenter valda bland följande: lägre alkyl, lägre alkoxi, hydroxi, halogen, halogen(lägre)alkyl, amino, nitro, karboxiamido, fenyl(lägre)alkoxi, där fenyl-gruppen eventuellt är substituerad med en eller flera lägre alkyler, lägre alkoxi eller halogener, eller (lägre)al-25 kylamino, di(lägre)alkylamino eller acylamino, Z1 - Z2 är ch2-ch, nr2-ch, o-ch, s-ch, ch2-n, o-n, S-N, NR2-N, CH-NR2 eller N-NR2, där R2 är väte, (lägre)alkyl . eller fenyl eller fenyl(lägre)alkyl, där fenylgrupperna eventuellt är substituerade med en eller flera alkyl-, 30 lägrealkoxi- eller halogensubstituenter, Z3 - Z4 är CH=CH, 0-CH2 eller N=CH, Z5 är N eller CH, Z6 är 0, S eller NH, W betecknar syre eller svavel. 28 95031 Y är NH eller 0, B betecknar en mättad azacyklisk ring med formeln /^7\ 3 _/ fCH,)n N-RJ (II)
5. My där n är 2, 3 eller 4, och R3 är väte eller (lägre)alkyl; eller 10 _ _J 7\ \^a2]2 J ^111) 15 eller en N-oxid därav, kännetecknat av att a) ett isocyanat eller isotiocyanat med formeln (VII) A-CO-NCW (VII) 20 där A och W betecknar samma som ovan, reageras med en amin eller alkohol med formeln (VIII) B-YH (VIII) 25 där B och Y betecknar samma som ovan, eller b) en förening med den allmänna formeln (IX) A-CO-NHCWNH2 (IX) 30 där A och W betecknar samma som ovan reageras med en amin med den allmänna formeln B-NH2 (X) II 29 95031 där B betecknar samma som ovan, för att erhälla en fö-rening med formeln (I), där Y är NH, eller c) en förening med formeln
5 NH2CWY-B (xi) där Y, W och B betecknar samma som ovan, reageras med ett acylerande ämne, som innehäller gruppen A-CO-, där A betecknar samma som ovan, eller 10 d) en förening med formeln (1), där B betecknar radikalen (III), oxlderas för att erhälla en förening med formeln (I), där B betecknar N-oxlden 1 radikalen (III), eller e) en bas med formeln (I) omvandlas tili ett f ar-15 maceutiskt godtagbart syraadditionssalt därav, eller f) en racemlsk förening med formeln (I) sönderde-las 1 sinä optiska Isomerer.
2. Förfarande enligt patentkrav 1, känne-t e c k n a t av att A är en grupp med formeln 20 : "rv 6 (XIV) 25 där R6 - R9 var för sig betecknar väte eller den 1 patentkrav 1 deflnierade substltuenten R1. : 3. Förfarande enligt patentkrav 2, känne- tecknat av att R6 är lägre alkoxl och R7, R8 och R9 30 är väte, eller R6 är lägre alkyloxi eller cyklo(lägre)alkyl (lägre)alkyloxi, R7 är väte, R® är amino eller lägre alkylamino och R9 är halogen, eller R7 och R9 är klor och R6 och R® är väte. 30 95031
4. Förfarande enligt nägot av de föregäende paten tkraven, kännetecknat av att B är tropan- 3-yl eller k±nuklidin-3-yl.
5. Förfarande enligt patentkrav 1, k ä n n e -5 tecknat av att A betecknar en radikal med formeln (a), där R1 är väte eller en halogen(lägre)alkyllägre alkoxi-, lägre alkyl-, amino-, (lägre)alkylamino-, di(lägre )alkylamino- eller (lägre)alkanoylaminosubstituent, eller A betecknar en radikal med formeln (b), där Z5 är CH 10 och R1 betecknar väte eller en eller flera lika eller olika substituenter valda bland följande: lägre alkyl, lägre alkoxi, hydroxi, halogen, halogen(lägre)alkyl, amino, nitro, karboxiamido(lägre)alkylamino, di(lägre)alkylamino eller (lägre)alkanoylamino. 15 6. Förfarande enligt patentkrav 1, känne tecknat av att produkten är N-[[[1-azabicyklo-[2.2.2]oktan-3-yl]amino]karbonyl]-2-metoxibensamid eller ett farmaceutiskt godtagbart sait därav.
7. Förfarande enligt patentkrav 1, k ä n n e -20 tecknat av att produkten är N-[ [[ l-azabicyklo[2.2.2]oktan-3-yl]amino]karbonyl]-3,5-diklorbensamid, ( endo ) -N- ( 3,5-diklorbensoyl) -0- (8-metyl-8-azabicyklo- [3.2.1]okt-3-yl)karbamat,
25 N-[[[l-azabicyklo[2.2.2]oktan-3-yl]amino]karbonyl]-3-tri- fluormetylbensamid, N-[ [ [l-azabicyklo[2.2.2]oktan-3-yl]amino]karbonyl] -4-me-: toxibensamid, N- [ [ [l-azabicyklo[2.2.2]oktan-3-yl]amino]karbonyl]nafta-30 len-2-karboxiamid, N- [ [ [l-azabicyklo[2.2.2]oktan-3-yl]amino]karbonyl] -2-fu-rankarboxiamid, N-[[[l-azabicyklo[2.2.2]oktan-3-yl]amino]karbonyl]2,6-di-metylbensamid, II 31 95031 N-[[[l-azabicyklo[2.2.2]oktan-3-yl]amino]karbonyl]-2-tio-fenkarboxiamid, N-[[[l-azabicyklot2.2.2]oktan-3-yl]amino]karbonyl]-2-£luorbensamid,
5 N-[[[l-azabicyklo[2.2.2]oktan-3-yl]amino]karbonyl]-2- etoxibensamid, N-[[[l-azabisyklo[2.2.2]oktan-3-yl]amino]karbonyl]-2-iso-propoxlbensamid, 2-allyloxi-N- [ [ [ 1-azabicyklo [2.2.2] oktan-3-yl ] amino] karbo-10 nyl]bensamid, N- [ [ [ 1-azabicyklo [2.2.2] oktan-3-y1 ] amino ] karbonyl ]-2-pyri-dinkarboxiamidi, (endo)-N-[[[8-metyl-8-azabicyklo[3.2.1]oktan-3-yl]amino]-karbonyl-2-metoxibensamid,
15 N-[ [ [1-azabicyklo [2.2.2] oktan-3-yl] amino] karbonyl] -2-me- tylbensamid, N-[[[1-azabicyklo[2.2.2]oktan-3-yl]amino]karbonyl]-2-((cyklopropyl)metoxi)bensamid, (S)—N—[[[1-azabicyklo[2.2.2]oktan-3-yl]amino]karbonyl]-2-20 metoksibensamid, (R)-N-[[[1-azabicyklo[2.2.2]oktan-3-yl]amino]karbonyl]-2-metoxibensamid, i eller ett farmaceutiskt godtagbart sait av dessa. »
FI885917A 1987-12-24 1988-12-21 Förfarande för framställning av heterocykliska föreningar FI95031C (sv)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB8730193 1987-12-24
GB878730193A GB8730193D0 (en) 1987-12-24 1987-12-24 Heterocyclic compounds
GB888819728A GB8819728D0 (en) 1988-08-19 1988-08-19 Heterocyclic compounds
GB8819728 1988-08-19

Publications (3)

Publication Number Publication Date
FI885917A FI885917A (sv) 1989-06-25
FI95031B true FI95031B (sv) 1995-08-31
FI95031C FI95031C (sv) 1995-12-11

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US (2) US4983600A (sv)
EP (2) EP0361629B1 (sv)
JP (1) JP2588265B2 (sv)
KR (1) KR970009588B1 (sv)
AT (2) ATE107304T1 (sv)
AU (1) AU611976B2 (sv)
CA (1) CA1334095C (sv)
DE (2) DE3864807D1 (sv)
DK (2) DK710488A (sv)
ES (2) ES2051867T3 (sv)
FI (1) FI95031C (sv)
GB (1) GB2213816B (sv)
GR (1) GR3002701T3 (sv)
HU (1) HU204267B (sv)
IE (2) IE63474B1 (sv)
IL (1) IL88644A (sv)
PH (1) PH27437A (sv)
PT (1) PT89286B (sv)

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EP0361629A3 (en) 1990-06-13
ATE107304T1 (de) 1994-07-15
KR890009923A (ko) 1989-08-04
IE881029L (en) 1989-06-24
IE883661L (en) 1989-05-24
IE62231B1 (en) 1995-01-11
JP2588265B2 (ja) 1997-03-05
IE63474B1 (en) 1995-04-19
EP0323077A1 (en) 1989-07-05
ES2053959T3 (es) 1994-08-01
DK82793A (da) 1993-07-08
DK82793D0 (da) 1993-07-08
HU204267B (en) 1991-12-30
KR970009588B1 (ko) 1997-06-14
ES2051867T3 (es) 1994-07-01
DK710488A (da) 1989-06-25
JPH01203365A (ja) 1989-08-16
US4983600A (en) 1991-01-08
AU2670288A (en) 1989-06-29
GB2213816B (en) 1991-05-08
DE3850255D1 (de) 1994-07-21
DE3850255T2 (de) 1994-09-22
GB8829164D0 (en) 1989-01-25
FI95031C (sv) 1995-12-11
EP0323077B1 (en) 1991-09-11
AU611976B2 (en) 1991-06-27
PT89286B (pt) 1994-11-30
EP0361629B1 (en) 1994-06-15
US5106843A (en) 1992-04-21
CA1334095C (en) 1995-01-24
PH27437A (en) 1993-07-02
EP0361629A2 (en) 1990-04-04
GR3002701T3 (en) 1993-01-25
GB2213816A (en) 1989-08-23
DK710488D0 (da) 1988-12-20
DE3864807D1 (de) 1991-10-17
HUT53101A (en) 1990-09-28
PT89286A (pt) 1989-12-29
IL88644A0 (en) 1989-07-31
FI885917A (sv) 1989-06-25
IL88644A (en) 1993-05-13
ATE67200T1 (de) 1991-09-15

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