FI65243B - Foerfarande foer framstaellning av heterocykliska derivat av guanidin - Google Patents

Foerfarande foer framstaellning av heterocykliska derivat av guanidin Download PDF

Info

Publication number
FI65243B
FI65243B FI770864A FI770864A FI65243B FI 65243 B FI65243 B FI 65243B FI 770864 A FI770864 A FI 770864A FI 770864 A FI770864 A FI 770864A FI 65243 B FI65243 B FI 65243B
Authority
FI
Finland
Prior art keywords
formula
compound
alkyl
methyl
phenyl
Prior art date
Application number
FI770864A
Other languages
English (en)
Finnish (fi)
Other versions
FI770864A (sv
FI65243C (fi
Inventor
Chris Royce Rasmussen
Original Assignee
Mcneilab Inc
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 Mcneilab Inc filed Critical Mcneilab Inc
Publication of FI770864A publication Critical patent/FI770864A/fi
Publication of FI65243B publication Critical patent/FI65243B/fi
Application granted granted Critical
Publication of FI65243C publication Critical patent/FI65243C/fi

Links

Classifications

    • 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
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • 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
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/18—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings 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
    • C07D223/12—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
    • C07D317/66—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Diabetes (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (3)

1. Förfarande för framställning av terapeutiskt användbara heterocykliska derivat av guanidin med formeln Ro_(CH9) I 2 nNR Rj, r2-\N/:!,-C-N (I) X I 5 R1 och deras farmaceutiskt godtagbara syraadditions- och kvaternära salter, i vilken formel n ärheltalet 1, 2 eller 3; R^ är väte, C^-Cg-alkyl, Cg-Cg-cykloalkyl, Cg-Cg-alken-2-yl, hydroxi-lägre-alkyl, aralkyl eller aryl; R2 är väte, C^-Cg-alkyl eller aryl; Rg är väte, C^-Cg-alkyl eller aryl; R^ är väte, metyl eller etyl; Rg är C^-C^-alkyl, Cg-C^-sykloalkyl, aralkyl eller aryl; eller gruppen Λ -N ^R5 betecknar en 3- tili 7-ledad mättad heterocyklisk ring, väri da -NR^Rg betecknar en 6-ledad ring, (i) kan dessutom ingä en syre-eller svavelatom eller en ytterligare kväveatom, vilken kan vara substituerad med lägre-alkyl, fenyl eller bensyl, eller (ii) nämnda ring kan vara substituerad med lägre-alkyl vid en kolatom annan än en kolatom liggande omedelbart intill kväveatomen som är bunden vid karboximidamidgruppen, t.ex. pyrrolidinyl, piperidino, morfolino, tiomorfolino, 2,6-di-lägre-alkyl-morfolino (företrädesvis 2,6-di-metyl-morfol.ino) , 4-lägre-alkyl-piperazinyl (företrädesvis 4-metyl-piperazinyl), 4-fenyl-piperazinyl; R är C^-C^g-alkyl, Cg-Cg-cyklo-alkyl, C^-C^g-bicykloalkyl, C^-C^g-bicykloalkenyl, Cg-C1Q-tricyklo-alkyl, 1-adamantylmetyl, Cg-C^g-tricykloalkenyl, aryl-C-^-C^-alkyl, väri arylgruppen är fenyl eller naftyl; difenyl-C^-C^-alkyl; naftyl; fenyl; metylendioxifenyl; fenyl substituerad med 1-3 substituenter av följande: halogen, lägre alkyl och lägre alkoxi; och fenyl substituerad med amino, dimetylamino, metyletylamino, dietylamino, lägre-alkanoylamino, tio-lägre-alkyl, sulfinyl-lägre-alkyl, trifluormetyl, hydroxi, bensyloxi, lägre-alkanoyloxi, lägre-alkanoyl eller nitro; 57 6 5 2 4 3 eller 3-pyridyl, som i sinä ringkolatomer är substituerad med 1-2 halogen-, lägre-alkyl- eller lägre alkoxisubstituenter, k ä n -netecknat därav, att man a) omsätter en förening med formeln r -© Ro_l ,cUi.»x YÖ (III) Ni- R! väri X är metoxi eller etoxi och Y ^ är BF^ eller OSC>2 med en förening med formeln NR h2n-c-nr4r5 (IV) i ett lämpligt vattenfritt organiskt lösningsmedel, för framställ-ning av en förening med formeln R3 (CH2 n NR · HY (V) i R1 och omvandlar förening V till motsvarande basform (I) pä ett i och för sig känt sätt, säsom genom behandling med ett lämpligt alkali; eller b) omsätter en förening med formeln R-_(CH_) o Z n Ro—s (lägre-alkyl) © _ I Y,® Ri S8 65 2 4 3 väri är en anjon, säsom jO; OSO^ A metylsulfat; tosylat eller mesylat, med en förening motsvarande ovan definierade formed (IV), i ett vattenfritt organiskt lösningsmedel, och omvand-lar det erhällna saltet av föreningen med formeln (I) tili motsvarande basform (I) pä ett i och för sig känt sätt, säsom genom benandling med alkali; eller c) omsätter den fria basformen av föreningen med formeln (III) (väri är väte), som har formeln *3 | <CH2>n i <IX) —v. Λ— x
2 KY med föreningen med formeln (IV) i ett vattenfritt organiskt lösningsmedel, företrädesvis vid förhöjd temperatur, för framställning av en förening med formeln R3 j <CH2)nNR R3 —j—!CH2,n NR r2 -Ln-C-NR.Rj tautoj^r^ ^ (X) I ----------- H X eller d) omsätter en förening med formeln -ιΘ R [ ,‘Luu OMe ΟΞΟ,Μθ U (XII) 2 3 | L 59 6 5 2 4 3 med en förening med formeln (IV) i ett vattenfritt organiskt lösningsmedel, företrädesvis vid 25°-100°C för framställning av motsvarande metylsulfatsalt av föreningen med formeln (I), vil-ket kan omvandlas tili fri bas med formeln (I) genom behandling med alkali; eller e) omsätter en förening med formeln R3-r-(CH2>n „ I . , (Xlla) R2__1 y 0 lägre-alkyl 0 lägre-alkyl R1 med en förening med formeln (IV) i ett vattenfritt organiskt lösningsmedel för framställning av fria basformen med formeln (I); eller f) omsätter en förening med formeln
3 V" Θ R —^ Cl Cl I© L Ri med en förening med formeln (IV) i ett vattenfritt aprotiskt lösningsmedel, företrädesvis i ett aromatiskt kolväte, för framställning av en förening med formeln (I), eller g) omsätter en förening med formeln R3 Τ' (CH2)n SR1 r2 -J^n/J=n-c=nr . HZ (XVII) R1
FI770864A 1976-03-19 1977-03-18 Foerfarande foer framstaellning av heterocykliska derivat av guanidin FI65243C (fi)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US66838676A 1976-03-19 1976-03-19
US66838676 1976-03-19
US75258876A 1976-12-20 1976-12-20
US75258876 1976-12-20

Publications (3)

Publication Number Publication Date
FI770864A FI770864A (sv) 1977-09-20
FI65243B true FI65243B (fi) 1983-12-30
FI65243C FI65243C (fi) 1984-04-10

Family

ID=27099888

Family Applications (1)

Application Number Title Priority Date Filing Date
FI770864A FI65243C (fi) 1976-03-19 1977-03-18 Foerfarande foer framstaellning av heterocykliska derivat av guanidin

Country Status (21)

Country Link
JP (1) JPS52136168A (sv)
AT (1) AT356669B (sv)
AU (1) AU517804B2 (sv)
CA (1) CA1100494A (sv)
CH (4) CH635073A5 (sv)
DD (1) DD130242A5 (sv)
DE (1) DE2711757A1 (sv)
DK (1) DK119477A (sv)
ES (1) ES457010A1 (sv)
FI (1) FI65243C (sv)
FR (1) FR2361366A1 (sv)
GB (1) GB1573532A (sv)
GR (1) GR60780B (sv)
IE (1) IE44792B1 (sv)
IL (1) IL51694A (sv)
NL (1) NL7703011A (sv)
NO (1) NO148524C (sv)
NZ (1) NZ183570A (sv)
PH (1) PH16561A (sv)
RO (1) RO71209A (sv)
SE (1) SE423628B (sv)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995009619A2 (en) * 1993-10-04 1995-04-13 The Wellcome Foundation Limited Substituted urea and isothiourea derivatives as no synthase inhibitors
US4101659A (en) * 1977-08-29 1978-07-18 Mcneil Laboratories, Incorporated Benzhydryl guanidines
ZA793186B (en) * 1978-07-06 1981-02-25 Duphar Int Res New urea and thiourea compounds, method of preparing the new compounds, as well as insecticidal compositions on the basis of these compounds
ATE2075T1 (de) * 1979-04-20 1983-01-15 Beecham Group Plc Oxazolin- und thiazolin-derivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zusammensetzungen.
JPS55160764A (en) * 1979-05-29 1980-12-13 Ciba Geigy Ag Guanidine* its manufacture and pharmaceutic medicine containing same
EP0028883A3 (en) * 1979-11-10 1981-06-03 Beecham Group Plc Benzimidazoline derivatives, processes for their preparation and pharmaceutical compositions containing them
JPH06198992A (ja) * 1992-11-30 1994-07-19 Shinko Seisakusho Co Ltd 紙葉類搬送装置
US5885985A (en) * 1993-03-23 1999-03-23 Astra Aktiebolag Guanidine derivatives useful in therapy
US6297276B1 (en) 1993-10-04 2001-10-02 Glaxosmithkline Substituted urea and isothiourea derivatives as no synthase inhibitors
US6225305B1 (en) 1993-10-04 2001-05-01 Glaxo Wellcome Inc. Substituted urea and isothiorea derivatives as no synthase inhibitors
US6090846A (en) * 1994-06-01 2000-07-18 Glaxo Wellcome Inc. Substituted urea and isothiourea derivatives as no synthase inhibitors

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2205744A1 (de) * 1972-02-08 1973-08-09 Thomae Gmbh Dr K Neue durch einen guanidinylidenrest substituierte heterocyclen und verfahren zu ihrer herstellung
GB1414048A (en) * 1972-03-17 1975-11-12 Mcneilab Inc Pyrrolidylidene piperidylidene and hexahydroazepinylidene ureas
US3803170A (en) * 1972-08-11 1974-04-09 Richardson Merrell Inc 2-((1-benzylcyclopentyl)imino)pyrrolidine

Also Published As

Publication number Publication date
IE44792L (en) 1977-09-19
IL51694A0 (en) 1977-05-31
CH636084A5 (en) 1983-05-13
FR2361366A1 (fr) 1978-03-10
FI770864A (sv) 1977-09-20
CA1100494A (en) 1981-05-05
IE44792B1 (en) 1982-04-07
DK119477A (da) 1977-09-20
CH635073A5 (en) 1983-03-15
IL51694A (en) 1982-01-31
SE7703114L (sv) 1977-09-20
FR2361366B1 (sv) 1984-03-02
AU2335177A (en) 1978-09-21
NO148524C (no) 1983-10-26
SE423628B (sv) 1982-05-17
JPS6327342B2 (sv) 1988-06-02
ATA190677A (de) 1979-10-15
RO71209A (ro) 1981-11-04
AT356669B (de) 1980-05-12
GR60780B (en) 1978-08-28
PH16561A (en) 1983-11-18
GB1573532A (en) 1980-08-28
JPS52136168A (en) 1977-11-14
CH632994A5 (en) 1982-11-15
FI65243C (fi) 1984-04-10
NO770959L (no) 1977-09-20
NZ183570A (en) 1979-06-08
DD130242A5 (de) 1978-03-15
NL7703011A (nl) 1977-09-21
ES457010A1 (es) 1978-07-16
CH634557A5 (en) 1983-02-15
NO148524B (no) 1983-07-18
AU517804B2 (en) 1981-08-27
DE2711757A1 (de) 1977-09-22

Similar Documents

Publication Publication Date Title
Petersen et al. Synthesis and hypotensive activity of N-alkyl-N''-cyano-N'-pyridylguanidines
CA1190224A (en) Derivatives of 1,2-diamino-cyclobutene-3,4-dione as potent histamine h.sub.2-antagonists
US3736331A (en) Isothioureas
US4101659A (en) Benzhydryl guanidines
FI65243B (fi) Foerfarande foer framstaellning av heterocykliska derivat av guanidin
EP0445796A2 (de) Essigsäurederivate
NL193539C (nl) Nieuwe fenylaminoguanidinederivaten en een geneesmiddel met antiarrhythmische werking dat een dergelijk derivaat bevat.
US3391189A (en) Nu-allyl-guanidines and salts thereof
DD294023A5 (de) Therapeutische mittel
US2704757A (en) 5-hydroxy-3, 4, 5, 6-tetrahydropyriminines
Ainsworth et al. 3-Aminoalkyl-1, 2, 4-triazoles
CS225804B2 (cs) Způsob výroby heterocyklických derivátů guanidinu
CA1065874A (en) 3-substituted indoles and precursors therefor
FI64800C (fi) Foerfarande foer framstaellning av isotiourinaemnederivat anvaendbara som histamin h2-antagonister
FI69069B (fi) Foerfarande foer framstaellning av terapeutiskt anvaendbara n-yan-n&#39;-(2-((4-metyl-5-imidazolyl)metyltio)etyl)-n&#34;-alkyny lganidiner
Elpern et al. Strong analgesics. The preparation of some ethyl 1-anilinoalkyl-4-phenylpiperidine-4-carboxylates
JPH06135925A (ja) ヒスタミンｈ▲２▼−受容体拮抗活性をもつ置換３，４−ジアミノ−１，２，５−チアジアゾール用中間体
FI89918B (fi) Foerfarande foer framstaellning av ett terapeutiskt anvaendbart kristallint 2-(1-pentyl-3-guanidino)-4-(2-metyl-4-imidazolyl)tiazoldihydrokloridtrihydrat
KR810000058B1 (ko) 구아니딘의 헤테로 고리화합물 유도체의 제조방법
US2613225A (en) alpha-phenylamino-propionic acid amidine and its salts
FI58125C (fi) Foerfarande foer framstaellning av 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolin med blodtryckssaenkande vekan
US3311639A (en) Preparation of hydrochloride salts of s-methyl-isothiourea derivatives
PL98607B1 (pl) Sposob wytwarzania nowych,czwartorzedowych soli amoniowych
KR790001525B1 (ko) 치환된 인돌유도체의 제법
US3489758A (en) 1-((2,6-dimethylpiperidino)lower alkyl)-3-((1-phenylcyclobutyl)carbonyl)ureas

Legal Events

Date Code Title Description
MM Patent lapsed

Owner name: MCNEIL, LABORATORIES INC