FI92205B - Förfarande för framställning av terapeutiskt användbara N-pyrrolo- och pyrido /3,2,1,-j k/ /1,4/ bensodiazepinyl-N'-arylurea och tioureaderivat - Google Patents

Förfarande för framställning av terapeutiskt användbara N-pyrrolo- och pyrido /3,2,1,-j k/ /1,4/ bensodiazepinyl-N'-arylurea och tioureaderivat Download PDF

Info

Publication number
FI92205B
FI92205B FI904731A FI904731A FI92205B FI 92205 B FI92205 B FI 92205B FI 904731 A FI904731 A FI 904731A FI 904731 A FI904731 A FI 904731A FI 92205 B FI92205 B FI 92205B
Authority
FI
Finland
Prior art keywords
protons
proton
formula
phenyl
mmol
Prior art date
Application number
FI904731A
Other languages
English (en)
Finnish (fi)
Other versions
FI904731A0 (sv
FI92205C (sv
Inventor
Jean-Louis Junien
Alain Pierre Calvet
Francois Joseph Roman
Yves Robert Alain Pascal
Xavier Bernard Louis Pascaud
Original Assignee
Jouveinal Sa
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.)
Filing date
Publication date
Application filed by Jouveinal Sa filed Critical Jouveinal Sa
Publication of FI904731A0 publication Critical patent/FI904731A0/sv
Application granted granted Critical
Publication of FI92205B publication Critical patent/FI92205B/sv
Publication of FI92205C publication Critical patent/FI92205C/sv

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
    • C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
    • C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
    • C07D243/20—Nitrogen atoms
    • 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
    • C07D471/06—Peri-condensed systems
    • 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
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • 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
    • 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
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • 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
    • 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
    • C07D487/06—Peri-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Child & Adolescent Psychology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Claims (5)

1. Förfarande för framställning av terapeutiskt användbara N-pyrrolo- och pyrido [3,2,1-j k] [l,4]benso-5 drazepinyl-N'arylurea- och- tioureaderivat med formeln (I), (CH2)a R9—if- I )—N - C - N - Ar
10 INI (I) V Rc 15 där R, är väte eller halogen; symbolerna Ra, Rb och Rc oberoende av varandra be-tecknar väte, halogen, lägre alkyl, nitro eller trifluor-metyl;
20 R12 är en syreatom eller en svavelatom; Ar är fenyl, som eventuellt är mono- eller disub-stituerad med lika eller olika grupper, som betecknar lägre alkyl, (lägre alkoxi)-karbonyl, aminosulfonyl, nitro, trifluormetyl, eller ifali R12 är en svavelatom, halogen; 25 eller Ar är naftyl, pyridyl eller kinolinyl; och a är 2 eller 3; kännetecknat därav, att (A) för framställning av racemiska föreningar: (i) omsätts en racemisk amin, som har formeln (II): 30 (CH2)a Sm R9 -*f- I \-NH2
35 J --Ά Rb Rc II (ii) 92205 77 där Ra, Rb, Rc, R9 och a är ovan definierade, med ett arylisocyanat, som har formeln Ar-N=O0, där Ar är ovan definierad, för erhällande av en racemisk bensodiazepin (Ia), som har formeln (I), där Rl2 är syre; eller 5 (ii) omsätts den racemiska aminen (II), där R,, Rb, Rc, R, och a är ovan definierade, med ett arylisotiocyanat, som har formeln Ar-N-C=S, där Ar är ovan definierad, för erhällande av en racemisk bensodiazepin (Ie), som har formeln (I), där R12 är svavel; och 10 (B) för framställning av enantiomera former används motsvarande enantiomerer (II) i förfaranden (i) och (ii) för erhällande av enantiomera former av bens-odiazepiner med formlerna (Ia) och (Ie).
2. Förfarande enligt patentkravet 1, k ä n n e -15 tecknat därav, att man framställer (4R,S)-N-(3-oxo- 6- fenyl-l,2,3,4-tetrahydro-pyrrolo[3,2, 1-j,k]bensodiaze-pin[l,4]-4-yl)-N'-(3-metylfenyl)urea och en (5R)-isomer därav.
3. Förfarande enligt patentkravet 1, k ä n n e -20 tecknat därav, att man framställer (5R,S)-N-(4-oxo- 7- fenyl-l, 2,3,3a, 4,5-hexahydro-pyrido[3,2,1- j , k]bensodiazepin [1,4]-5-yl)-N'-(3-metylfenyl)urea och en (5R)-isomer därav.
4. Förfarande enligt patentkravet 1, k ä n n e -25 tecknat därav, att man framställer (5R,S)-N-(4-oxo- 7-fenyl-l, 2,3,3a, 4,5-hexahydro-pyrido[3,2,1-j , k]bensodiazepin! 1 ,4]-5-yl)-N'-(4-nitrofenyl)urea.
5. Förfarande enligt patentkravet 1, känne-tecknat därav, att man framställer ( 5R,S)-N-(4-oxo- 30 7-fenyl-l, 2,3,3a, 4, 5-hexahydro-pyrido[3,2,1-j , k]bensodi- azepintl,4]-5-yl)-N'-(4-bromfenyl)tiourea, och en optisk isomer därav, samt en (5R)-isomer därav.
FI904731A 1989-09-28 1990-09-26 Förfarande för framställning av terapeutiskt användbara N-pyrrolo- och pyrido /3,2,1,-j k/ /1,4/ bensodiazepinyl-N'-arylurea och tioureaderivat FI92205C (sv)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8912700 1989-09-28
FR8912700A FR2652352A1 (fr) 1989-09-28 1989-09-28 Benzodiazepines, leur procede et intermediaires de preparation et leurs applications en therapeutique.

Publications (3)

Publication Number Publication Date
FI904731A0 FI904731A0 (sv) 1990-09-26
FI92205B true FI92205B (sv) 1994-06-30
FI92205C FI92205C (sv) 1994-10-10

Family

ID=9385901

Family Applications (1)

Application Number Title Priority Date Filing Date
FI904731A FI92205C (sv) 1989-09-28 1990-09-26 Förfarande för framställning av terapeutiskt användbara N-pyrrolo- och pyrido /3,2,1,-j k/ /1,4/ bensodiazepinyl-N'-arylurea och tioureaderivat

Country Status (14)

Country Link
US (1) US5082937A (sv)
EP (1) EP0420716A3 (sv)
JP (1) JPH03120278A (sv)
KR (1) KR910006244A (sv)
AU (1) AU624991B2 (sv)
CA (1) CA2026123A1 (sv)
FI (1) FI92205C (sv)
FR (1) FR2652352A1 (sv)
IE (1) IE903300A1 (sv)
IS (1) IS3632A7 (sv)
NO (1) NO174774C (sv)
NZ (1) NZ235104A (sv)
PT (1) PT95428A (sv)
ZA (1) ZA906939B (sv)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2630440B1 (fr) * 1988-04-25 1991-09-20 Jouveinal Sa Benzodiazepines, leur procede et intermediaires de preparation et leurs applications en therapeutique
US5248679A (en) * 1988-09-09 1993-09-28 Fujisawa Pharmaceutical Co., Ltd. Tricyclic compounds
PH26955A (en) * 1989-03-08 1992-12-03 Kali Chemie Pharma Gmbh Novel 1,7-fused 1H-indole-2-carboxylic acid N-(1,4-benzodiazepin-3-YL) amides
US5250679A (en) * 1991-10-18 1993-10-05 Genentech, Inc. Nonpeptidyl platelet aggregation inhibitors having specificity for the GPIIb III.sub. receptor
US5565449A (en) * 1991-10-18 1996-10-15 Genentech, Inc. Nonpeptidyl integrin inhibitors having specificity for the GPIIb IIIa receptor
GB2271354A (en) * 1992-10-07 1994-04-13 Merck Sharp & Dohme Tricyclic derivatives of benzodiazepines
WO1996006617A1 (en) * 1994-08-30 1996-03-07 Fujisawa Pharmaceutical Co., Ltd. Liposome preparation
FR2725719B1 (fr) * 1994-10-14 1996-12-06 Jouveinal Inst Rech Diazepino-indoles inhibiteurs de phosphodiesterases iv
FR2746800B1 (fr) * 1996-03-29 1998-06-05 Jouveinal Inst Rech Diazepino-indoles inhibiteurs de phosphodiesterases 4
AU3217501A (en) * 2000-03-03 2001-09-12 Pfizer Prod Inc Pyrazole ether derivatives as anti-inflammatory/analgesic agents
EP1161949A1 (en) 2000-06-09 2001-12-12 Warner-Lambert Company Use od diazepinoindoles for the treatment of chronic obstructive pulmonary disease

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2733371A (en) * 1970-04-14 1972-10-12 A. H. Robins Company, Incorporated 5, 7-DISUBSTITUTED-l, 9-ALKYLENE-l, 4-BENZODIAZEPIN-2 ONES
CA1332410C (en) * 1984-06-26 1994-10-11 Roger M. Freidinger Benzodiazepine analogs
US4820834A (en) * 1984-06-26 1989-04-11 Merck & Co., Inc. Benzodiazepine analogs
FR2630440B1 (fr) * 1988-04-25 1991-09-20 Jouveinal Sa Benzodiazepines, leur procede et intermediaires de preparation et leurs applications en therapeutique
IL91361A (en) * 1988-09-09 1994-10-07 Fujisawa Pharmaceutical Co Benzodiazepinone compounds [4,1] connected via positions 1 and 9 and carrying two transducers, processes for their preparation and pharmaceutical preparations containing them

Also Published As

Publication number Publication date
NO904222L (no) 1991-04-02
AU6204590A (en) 1991-04-11
NZ235104A (en) 1992-03-26
ZA906939B (en) 1991-06-26
US5082937A (en) 1992-01-21
EP0420716A2 (fr) 1991-04-03
NO174774B (no) 1994-03-28
FR2652352A1 (fr) 1991-03-29
JPH03120278A (ja) 1991-05-22
IS3632A7 (is) 1991-03-29
PT95428A (pt) 1991-05-22
NO904222D0 (no) 1990-09-27
KR910006244A (ko) 1991-04-27
FI904731A0 (sv) 1990-09-26
FR2652352B1 (sv) 1994-04-22
FI92205C (sv) 1994-10-10
CA2026123A1 (en) 1991-03-29
EP0420716A3 (en) 1991-12-18
IE903300A1 (en) 1991-04-10
NO174774C (no) 1994-07-06
AU624991B2 (en) 1992-06-25

Similar Documents

Publication Publication Date Title
ES2223537T3 (es) Gamma-carbolinas condensadas con heterociclos sustituidas.
JP4231290B2 (ja) セロトニンの作動薬および拮抗薬としての置換されたピリドインドール
FI91409C (sv) Förfarande och mellanprodukter för framställning av ny terapeutiskt användbara karbonylamino(tetrahydropyrrolo eller hexahydropyrido)/3,2,1-jk//1,4/bentsodiatsepinderivat
FI92205B (sv) Förfarande för framställning av terapeutiskt användbara N-pyrrolo- och pyrido /3,2,1,-j k/ /1,4/ bensodiazepinyl-N'-arylurea och tioureaderivat
CA1296730C (en) 6,7,8,9-tetrahydropyrido[1,2-a] indole derivatives
KR20210104833A (ko) 치환된 헤테로사이클 융합 감마-카르볼린 합성
JP3010558B2 (ja) 新規の１，７‐融合１ｈ‐インドール‐２‐カルボン酸‐ｎ‐（１，４‐ベンゾジアゼピン‐３‐イル）‐アミド、その製法及びこれを含有するコレシストキニン拮抗作用薬剤
Huff et al. Bioactive conformation of 1-arylpiperazines at central serotonin receptors
Brière et al. Regioselective reductions of various 3-aminosuccinimides; application to the synthesis of two heterocyclic systems
US5686449A (en) 1,5-benzodiazepines useful as gastrinor CCK-antagonists
KR20030069192A (ko) 세로토닌 수용체 효능제 및 길항제로서 치환된피라지노퀴녹살린 유도체
Kraus et al. A direct route to the pyrrolo [2, 1-c][1, 4] benzodiazepine ring system using aryl triflates
IE872930L (en) 2-aminoacetamide derivatives
Ennis et al. Structure-Activity Relationships in the 8-Amino-6, 7, 8, 9-tetrahydro-3H-benz [e] indole Ring System. Part 2: Effect of 8-Amino Nitrogen Substitution on Serotonin Receptor Binding and Pharmacology
Jeannin et al. Practical Syntheses of Functionalized 1-Oxo-L, 2, 3, 4-Tetrahydro-β-carboline-3-carboxylic Acid Esters
Massa et al. 5, 6‐Dihydro‐4H‐pyrrolo [1, 2‐a][1, 4] benzodiazepine‐4, 4‐diacetic acid diethyl ester, an useful synthon for the synthesis of new polycyclic nitrogen systems of pharmacological interest
US3968230A (en) Compositions containing benzodiazepindiones and method of use
CA2011658C (en) New 1,7-annelated 1h-indole-2-carboxylic acid-n-(1,4-benzodiazepin-3-yl) amides
KR850000261B1 (ko) 벤즈아제핀 유도체의 제조방법
Benedini et al. New organic nitrates. II. Synthesis of 2H‐pyrido [2, 3‐e]‐1, 3‐oxazine‐2, 4 (3H)‐diones, 2H‐pyrido [4, 3‐e]‐1, 3‐oxazine‐2, 4 (3H)‐diones, 2H‐pyrido [4, 3‐e]‐1, 3‐oxazin‐4 (3H)‐ones, 2H‐thieno [2, 3‐e]‐1, 3‐oxazin‐4 (3H)‐ones and 2H‐thieno [3, 4‐e]‐1, 3‐oxazin‐2, 4 (3H)‐diones
Fidalgo et al. BENZ [d] INDENO [l, Z-b1AZEPINES
EP0456196A1 (en) Pyrrolo,[2,3-b]indole-ketones and analogs, a process for their preparation and their use as medicaments
Lessor et al. Lead tetra-acetate oxidation of tetrahydrobenzazepine enamides: the synthesis of N-acyl substituted tetrahydro-3-benzazocin-2 (1 H)-ones. A chemical and crystallographic study
GB2249094A (en) Hetero-imidazodiazepine derivatives
WO1998023618A1 (en) 2,3,4,7-tetrahydropyridoindazole[1,4] benzodiazepine derivatives having antitumor activity

Legal Events

Date Code Title Description
FG Patent granted

Owner name: JOUVEINAL S.A.

BB Publication of examined application
MM Patent lapsed
MM Patent lapsed

Owner name: JOUVEINAL S.A.