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PL123449B1 - Process for preparing novel derivatives of 2-iminothiazoline - Google Patents

Process for preparing novel derivatives of 2-iminothiazoline Download PDF

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Publication number
PL123449B1
PL123449B1 PL1977223798A PL22379877A PL123449B1 PL 123449 B1 PL123449 B1 PL 123449B1 PL 1977223798 A PL1977223798 A PL 1977223798A PL 22379877 A PL22379877 A PL 22379877A PL 123449 B1 PL123449 B1 PL 123449B1
Authority
PL
Poland
Prior art keywords
formula
compound
optionally
alkyl
iminothiazoline
Prior art date
Application number
PL1977223798A
Other languages
Polish (pl)
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 filed Critical
Publication of PL123449B1 publication Critical patent/PL123449B1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings 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
    • C07D277/18—Nitrogen atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/39—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups
    • C07C205/42—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/43—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings 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
    • C07D277/16—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D277/38—Nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Neurology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biomedical Technology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Psychiatry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Neurosurgery (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Claims (2)

1. Zastrzezenia patentowe 1. Sposób wytwarzania nowych pochodnych 2-iminoUazolilny o wzorze 1, ewentualnie w postaci jego farmaceutycznie dopuszczalnej soli, znamienny tym, ze zwiazek o wzorze 2 poddaje sie reakcji ze zwiazkiem o wzorze 3, w którym Y' oznacza grupe 10 wodorotlenowa, po czym otrzymany produkt ewen¬ tualnie przeprowadza sie w sól. 2. Sposób otrzymywania nowych pochodnych 2-imi-notiazoliny o wzorze 1, ewentualnie w postaci jego farmaceutycznie dopuszczalnej soli, znamienny tym, ze zwiazek o wzorze 2 poddaje sie reakcja ze zwiazkiem o wzorze Y-CO-CH2-CH2-CO-Y, w któ¬ rym Y oznacza atom chloru, grupe o wzorze 4, -N3, (alkil Ci_4)-0-COO-, -OCH2CN, podstawnik o wzorze 5, 6, 7, 8, 9 lub o wzorze -0-(alkil Ci_4), po czym otrzymany produkt ewentualnie przepro¬ wadza sie w sól. o o f =N-CCH2CI-UC-N=($1 I I CH3 CH3 WZÓR \ r~S CN=NH ^ CK 3 WZÓR 2 a 0 o ri_ » if l L 2 CH3 WZÓR 3123 449 N02^0^~ ° " WZÓR 4 F F F F W20R 5 H OH oV4n OPh WZÓR S O-C \ NH N(GK alkil)2 WZÓR 8 O-C \ CH: 0[CHalkil)2 WZÓR 9 L 632594 O 100 200300 400 500600700800 pg. proteiny enzymu 2 ™ 80.000 60.000 2: ¦o o c ? » ^c o o c N O » O a o. tn * c 'a "o o. u» c h- Zt. o "o* a *^ i ^r A0.0C0 h 20.000 2 godz. &% 3godz 7 godz. 52% 51% 85% BW 36% 54% 53% 55% 8,1 8,1 12,5 25 25 25 68 68 63 Dawka doustna (mg/kg) * 1 królik /grupe Fig.l Fig.1. Claims 1. A process for the preparation of the new 2-imino-azolyl derivatives of formula 1, optionally in the form of a pharmaceutically acceptable salt thereof, characterized in that a compound of formula 2 is reacted with a compound of formula 3, wherein Y 'is a hydroxyl group the product obtained is then optionally salified. 2. A process for the preparation of new 2-imi-notiazoline derivatives of formula 1, optionally in the form of a pharmaceutically acceptable salt thereof, characterized in that a compound of formula 2 is reacted with a compound of formula Y-CO-CH2-CH2-CO-Y, where Y is a chlorine atom, a group of formula 4, -N3, (C1-4 alkyl) -O-COO-, -OCH2CN, a substituent of formula 5, 6, 7, 8, 9 or of the formula -O- (alkyl Ci_4) and the product obtained is then optionally salified. oof = N-CCH2CI-UC-N = ($ 1 II CH3 CH3 FORMULA \ r ~ S CN = NH ^ CK 3 FORMULA 2 a 0 o ri_ »if l L 2 CH3 FORMULA 3123 449 N02 ^ 0 ^ ~ °" FORMULA 4 FFFF W20R 5 H OH oV4n OPh FORMULA S OC \ NH N (GK alkyl) 2 FORMULA 8 OC \ CH: 0 [CHalkyl) 2 FORMULA 9 L 632594 O 100 200 300 400 500 600 700 800 pg enzyme protein 2 ™ 80.000 60.000 2: ¦ooc ? »^ Cooc NO» O a o. Tn * c 'a "o o. U» c h- Zt. o "o * a * ^ i ^ r A0.0C0 h 20,000 2 hours &% 3h 7 hours 52% 51% 85% BW 36% 54% 53% 55% 8.1 8.1 12.5 25 25 25 68 68 63 Oral dose (mg / kg) * 1 rabbit / group Fig. 1 Fig. 2. PL PL PL2. PL PL PL
PL1977223798A 1976-05-03 1977-04-30 Process for preparing novel derivatives of 2-iminothiazoline PL123449B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US68287676A 1976-05-03 1976-05-03

Publications (1)

Publication Number Publication Date
PL123449B1 true PL123449B1 (en) 1982-10-30

Family

ID=24741558

Family Applications (1)

Application Number Title Priority Date Filing Date
PL1977223798A PL123449B1 (en) 1976-05-03 1977-04-30 Process for preparing novel derivatives of 2-iminothiazoline

Country Status (24)

Country Link
JP (1) JPS52133981A (en)
AU (1) AU508889B2 (en)
BE (1) BE854172A (en)
CA (1) CA1078846A (en)
CH (1) CH629490A5 (en)
DE (1) DE2719577A1 (en)
DK (1) DK173777A (en)
ES (2) ES458237A1 (en)
FI (1) FI771285A (en)
FR (1) FR2350351A1 (en)
GB (1) GB1534242A (en)
HU (1) HU180504B (en)
IE (1) IE46011B1 (en)
IL (1) IL51935A (en)
IT (1) IT1082657B (en)
LU (1) LU77243A1 (en)
NL (1) NL7704322A (en)
NO (1) NO146061C (en)
NZ (1) NZ183941A (en)
PH (1) PH14030A (en)
PL (1) PL123449B1 (en)
SE (1) SE7704594L (en)
YU (1) YU111677A (en)
ZA (1) ZA772614B (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU188852B (en) * 1983-03-16 1986-05-28 Richter Gedeon Vegyeszeti Gyar Rt,Hu Process for producing thiazolidine derivatives active against gastric ulcer and intestinal ulcer
US5555162A (en) * 1994-04-26 1996-09-10 Sylvan R. Shemitz Designs, Inc. Compact fluorescent luminaire
USRE37310E1 (en) 1994-12-06 2001-08-07 Sylvan R. Shemitz Designs, Inc. Compact fluorescent luminaire
FR2748023B1 (en) * 1996-04-30 1998-07-24 Rhone Poulenc Chimie HYDROGENOFLUOROSULFONATES OF ORGANIC BASIS, THEIR USE TO RELEASE ORGANIC BASES FROM THEIR FLUORHYDRATE, THEIR PREPARATION PROCESS, COMPOSITIONS CONTAINING THEM

Also Published As

Publication number Publication date
PH14030A (en) 1980-12-12
CA1078846A (en) 1980-06-03
IT1082657B (en) 1985-05-21
AU508889B2 (en) 1980-04-03
NL7704322A (en) 1977-11-07
BE854172A (en) 1977-11-03
FR2350351A1 (en) 1977-12-02
YU111677A (en) 1983-01-21
HU180504B (en) 1983-03-28
NO146061B (en) 1982-04-13
FI771285A (en) 1977-11-04
GB1534242A (en) 1978-11-29
SE7704594L (en) 1977-11-04
IE46011L (en) 1977-11-03
CH629490A5 (en) 1982-04-30
DK173777A (en) 1977-11-04
LU77243A1 (en) 1977-12-13
IE46011B1 (en) 1983-01-26
NZ183941A (en) 1980-12-19
FR2350351B1 (en) 1979-03-02
ZA772614B (en) 1978-12-27
IL51935A0 (en) 1977-06-30
NO771375L (en) 1977-11-04
AU2463077A (en) 1978-11-02
ES468377A1 (en) 1978-12-16
DE2719577A1 (en) 1977-11-24
IL51935A (en) 1981-07-31
NO146061C (en) 1982-07-28
JPS52133981A (en) 1977-11-09
ES458237A1 (en) 1978-07-01

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