GB1499582A - Substituted tetrahydrobenzothiophenes - Google Patents

Substituted tetrahydrobenzothiophenes

Info

Publication number
GB1499582A
GB1499582A GB1592/75A GB159275A GB1499582A GB 1499582 A GB1499582 A GB 1499582A GB 1592/75 A GB1592/75 A GB 1592/75A GB 159275 A GB159275 A GB 159275A GB 1499582 A GB1499582 A GB 1499582A
Authority
GB
United Kingdom
Prior art keywords
formula
compound
nhr1
radical
reacting
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
GB1592/75A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB1499582A publication Critical patent/GB1499582A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/116—Heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/116—Heterocyclic compounds
    • A23K20/121—Heterocyclic compounds containing oxygen or sulfur as hetero atom
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/116—Heterocyclic compounds
    • A23K20/137—Heterocyclic compounds containing two hetero atoms, of which at least one is nitrogen
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/56—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
    • C07D333/66—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
    • C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
    • C07D333/80—Seven-membered rings

Abstract

The novel compounds correspond to the formula: <IMAGE> in which X, Y, Z, R1, R2, R3 and U have the meanings given in Claim 1. They are prepared by a) reacting one mol equivalent of a compound of the formula I or II, in which the -NR1-CX-NHR1 radical is replaced, or its acid addition salts with 1 to 1.5 mol equivalents of R2NCX or b) reacting one mol equivalent of an acid addition salt of a compound of the formula I or II, in which R2 and R3 denotes hydrogen and the -NR1-CX-NHR2 radical is replaced by -NHR1, with 1 to 1.5 mol equivalents of a compound of the formula MeNCX, in which Me denotes sodium or potassium, and isolating the product. The reaction (a) is carried out in water or an inert organic solvent at 0 to 100 DEG C. The reaction (b) is carried out in aqueous medium at pH = 5 to 7 and 10 to 80 DEG C. The novel compounds of the formulae I and II are administered orally to warm-blooded animals to improve the extent of the feed effect and to increase the growth rate. A supplementary feed for increasing the growth rate of poultry, fur-bearing animals and agricultural productive animals contains 70 to 99% by weight of an edible carrier and, as the remainder, a novel compound of the formula I or II.
GB1592/75A 1974-01-25 1975-01-14 Substituted tetrahydrobenzothiophenes Expired GB1499582A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US43682674A 1974-01-25 1974-01-25
US43682774A 1974-01-25 1974-01-25

Publications (1)

Publication Number Publication Date
GB1499582A true GB1499582A (en) 1978-02-01

Family

ID=27031116

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1592/75A Expired GB1499582A (en) 1974-01-25 1975-01-14 Substituted tetrahydrobenzothiophenes

Country Status (21)

Country Link
JP (1) JPS51125069A (en)
AT (1) AT353590B (en)
CA (1) CA1060899A (en)
CH (4) CH619703A5 (en)
CS (1) CS195276B2 (en)
DD (4) DD119790A5 (en)
DE (1) DE2501788C2 (en)
DK (1) DK22775A (en)
ES (1) ES434095A1 (en)
FR (1) FR2333801A1 (en)
GB (1) GB1499582A (en)
IE (1) IE42039B1 (en)
IL (1) IL46375A (en)
IN (1) IN141050B (en)
IT (1) IT1035548B (en)
LU (1) LU71711A1 (en)
NL (1) NL7500845A (en)
PH (1) PH14544A (en)
SE (1) SE421617B (en)
TR (1) TR18381A (en)
YU (1) YU36721B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007068330A1 (en) * 2005-12-16 2007-06-21 Merck Patent Gmbh 2-ADAMANTYLUREA DERIVATIVES AS SELECTIVE 11β-HSD1 INHIBITORS

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3994924A (en) * 1975-11-04 1976-11-30 American Cyanamid Company 4,5,6,7-Tetra hydro-7-oxobenzo(B)thien-4-yl isocyanate and isothiocyanate
FR2430231A1 (en) * 1978-07-04 1980-02-01 American Cyanamid Co 4,5,6,7-Tetra:hydro-benzo(b)thienyl-4 urea and 7-oxo deriv. compsn. - used for increasing growth of wool and ratio of sec. to prim. follicles in sheep, goats, llamas, rabbits and chinchilla
JPS6169772A (en) * 1984-12-04 1986-04-10 アメリカン　サイアナミッド　カンパニ− Tetrahydrobenzo(b)thiophene derivative, manufacture and animal growth acceleration

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007068330A1 (en) * 2005-12-16 2007-06-21 Merck Patent Gmbh 2-ADAMANTYLUREA DERIVATIVES AS SELECTIVE 11β-HSD1 INHIBITORS
EP1801098A1 (en) * 2005-12-16 2007-06-27 Merck Sante 2-Adamantylurea derivatives as selective 11B-HSD1 inhibitors
US8188288B2 (en) 2005-12-16 2012-05-29 Merck Patent Gesellschaft Mit Beschrankter Haftung 2-adamantylurea derivatives as selective 11beta-HSD1 inhibitors
EA017923B1 (en) * 2005-12-16 2013-04-30 Мерк Патент Гмбх 2-ADAMANTYLUREA DERIVATIVES AS SELECTIVE 11β-HSD1 INHIBITORS
US8466200B2 (en) 2005-12-16 2013-06-18 Merck Patent Gmbh 2-adamantylurea derivatives as selective 11β-HSD1 inhibitors

Also Published As

Publication number Publication date
CH619705A5 (en) 1980-10-15
JPS51125069A (en) 1976-11-01
AT353590B (en) 1979-11-26
DD125213A5 (en) 1977-04-06
IL46375A0 (en) 1975-04-25
SE7500793L (en) 1975-07-28
IN141050B (en) 1977-01-15
CA1060899A (en) 1979-08-21
ATA42675A (en) 1979-04-15
CH619704A5 (en) 1980-10-15
FR2333801B1 (en) 1982-07-09
FR2333801A1 (en) 1977-07-01
PH14544A (en) 1981-09-24
LU71711A1 (en) 1975-06-24
JPS6133830B2 (en) 1986-08-04
CH619949A5 (en) 1980-10-31
IE42039B1 (en) 1980-05-21
CS195276B2 (en) 1980-01-31
DK22775A (en) 1975-09-15
DE2501788A1 (en) 1975-07-31
IL46375A (en) 1982-04-30
IT1035548B (en) 1979-10-20
IE42039L (en) 1975-07-25
DD125211A5 (en) 1977-04-06
SE421617B (en) 1982-01-18
NL7500845A (en) 1975-07-29
YU17275A (en) 1982-06-18
DD119790A5 (en) 1976-05-12
DD125212A5 (en) 1977-04-06
ES434095A1 (en) 1977-05-16
DE2501788C2 (en) 1984-11-08
AU7691574A (en) 1976-07-01
TR18381A (en) 1977-05-01
YU36721B (en) 1984-08-31
CH619703A5 (en) 1980-10-15

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee