HRP20120466T1 - Derivati indol ona disupstituirani na položaju njihovo dobivanje i upotreba u terapiji - Google Patents
Derivati indol ona disupstituirani na položaju njihovo dobivanje i upotreba u terapiji Download PDFInfo
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- HRP20120466T1 HRP20120466T1 HRP20120466AT HRP20120466T HRP20120466T1 HR P20120466 T1 HRP20120466 T1 HR P20120466T1 HR P20120466A T HRP20120466A T HR P20120466AT HR P20120466 T HRP20120466 T HR P20120466T HR P20120466 T1 HRP20120466 T1 HR P20120466T1
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- 150000005625 indol-2-ones Chemical class 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 37
- 125000005843 halogen group Chemical group 0.000 claims abstract 23
- 125000003118 aryl group Chemical group 0.000 claims abstract 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract 16
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 8
- 125000001424 substituent group Chemical group 0.000 claims abstract 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 21
- 238000000034 method Methods 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 6
- -1 CN Chemical group 0.000 claims 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 208000027559 Appetite disease Diseases 0.000 claims 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- JYNKNVRRALLCEQ-UHFFFAOYSA-N 2-chloro-n-[5-chloro-3-(2-chlorophenyl)-2-oxo-1h-indol-3-yl]acetamide Chemical compound O=C1NC2=CC=C(Cl)C=C2C1(NC(=O)CCl)C1=CC=CC=C1Cl JYNKNVRRALLCEQ-UHFFFAOYSA-N 0.000 claims 1
- AGTXDVTUPNSEBX-UHFFFAOYSA-N 3-(4-chlorophenyl)-3-[[2-(4-ethylpiperazin-1-yl)acetyl]amino]-2-oxo-4-(trifluoromethyl)-1h-indole-6-carboxamide Chemical compound C1CN(CC)CCN1CC(=O)NC1(C=2C=CC(Cl)=CC=2)C2=C(C(F)(F)F)C=C(C(N)=O)C=C2NC1=O AGTXDVTUPNSEBX-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 206010033307 Overweight Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000037396 body weight Effects 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- IMOAOGGERDRWGD-UHFFFAOYSA-N n-[1-benzoyl-5,6-dichloro-3-(4-chlorophenyl)-2-oxoindol-3-yl]-2-(4-methylpiperazin-1-yl)acetamide Chemical compound C1CN(C)CCN1CC(=O)NC1(C=2C=CC(Cl)=CC=2)C2=CC(Cl)=C(Cl)C=C2N(C(=O)C=2C=CC=CC=2)C1=O IMOAOGGERDRWGD-UHFFFAOYSA-N 0.000 claims 1
- GFIXDZZIFFKZKX-UHFFFAOYSA-N n-[3-(4-chlorophenyl)-6-cyano-2-oxo-4-(trifluoromethyl)-1h-indol-3-yl]-2-(4-ethylpiperazin-1-yl)acetamide Chemical compound C1CN(CC)CCN1CC(=O)NC1(C=2C=CC(Cl)=CC=2)C2=C(C(F)(F)F)C=C(C#N)C=C2NC1=O GFIXDZZIFFKZKX-UHFFFAOYSA-N 0.000 claims 1
- GZMQEEHRXAENQK-UHFFFAOYSA-N n-[4,6-dichloro-1-ethyl-3-(2-methyl-1-benzofuran-5-yl)-2-oxoindol-3-yl]-2-(4-ethylpiperazin-1-yl)acetamide Chemical compound C1=C(Cl)C=C(Cl)C2=C1N(CC)C(=O)C2(C=1C=C2C=C(C)OC2=CC=1)NC(=O)CN1CCN(CC)CC1 GZMQEEHRXAENQK-UHFFFAOYSA-N 0.000 claims 1
- NDTOLICHDNPBOX-UHFFFAOYSA-N n-[4,6-dichloro-2-oxo-3-[4-(trifluoromethoxy)phenyl]-1h-indol-3-yl]-2-(4-ethylpiperazin-1-yl)acetamide Chemical compound C1CN(CC)CCN1CC(=O)NC1(C=2C=CC(OC(F)(F)F)=CC=2)C2=C(Cl)C=C(Cl)C=C2NC1=O NDTOLICHDNPBOX-UHFFFAOYSA-N 0.000 claims 1
- CDQNSIHAOJRPEP-UHFFFAOYSA-N n-[4,6-dichloro-3-(3,4-dichlorophenyl)-2-oxo-1h-indol-3-yl]-2-(4-ethylpiperazin-1-yl)acetamide Chemical compound C1CN(CC)CCN1CC(=O)NC1(C=2C=C(Cl)C(Cl)=CC=2)C2=C(Cl)C=C(Cl)C=C2NC1=O CDQNSIHAOJRPEP-UHFFFAOYSA-N 0.000 claims 1
- QIADWBMYPDIXLX-UHFFFAOYSA-N n-[5-chloro-3-(2-chlorophenyl)-2-oxo-1h-indol-3-yl]-2-(4-methylpiperazin-1-yl)acetamide Chemical compound C1CN(C)CCN1CC(=O)NC1(C=2C(=CC=CC=2)Cl)C2=CC(Cl)=CC=C2NC1=O QIADWBMYPDIXLX-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000004694 alkoxyaminocarbonyl group Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/40—Nitrogen atoms, not forming part of a nitro radical, e.g. isatin semicarbazone
-
- 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
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- 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
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- 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
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
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- General Chemical & Material Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
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Abstract
Spoj formule I naznačen time što predstavlja jednostruku ili dvostruku vezu X predstavlja N Ypredstavlja N ili CH gdje se podrazumijeva da najmanje jedan između X i Y predstavlja N Ar predstavlja arilnu ili heteroarilnu skupinu izborno supstituiranu s jednim ili više supstituenata kojimogu biti isti ili različiti i bira ih se između atoma halogena i C alkilnih C haloalkilnih perhalogen C alkilnih C alkoksi perhalogen C alkoksi i arilnih skupina R predstavlja atom vodika ili C alkilnu C O C alkilnu ili C O arilnu skupinu R R i R koji mogu biti isti ili različiti i nalaze se na bilo kojem od dostupnih položaja u fenilnoj jezgri neovisno predstavljaju atom vodika atom halogena CN OH C alkilnu skupinu izborno supstituiranu satomom halogena ili OH perhalogen C alkil C alkoksi perhalogen C alkoksi aminokarbonil
Claims (22)
1. Spoj formule (I):
[image]
naznačen time što:
[image]
predstavlja jednostruku ili dvostruku vezu,
X predstavlja -N<, -CH< ili
[image]
;
Y predstavlja >N- ili >CH-, gdje se podrazumijeva da najmanje jedan između X i Y predstavlja N;
Ar predstavlja arilnu ili heteroarilnu skupinu, izborno supstituiranu s jednim ili više supstituenata, koji mogu biti isti ili različiti i bira ih se između atoma halogena i (C1-6)alkilnih, (C1-6)haloalkilnih, perhalogen(C1-3)alkilnih, (C1-6)alkoksi, perhalogen(C1-3)alkoksi i arilnih skupina;
R1 predstavlja atom vodika ili (C1-6)alkilnu, - C(=O)(C1-6)alkilnu ili -C(=O)arilnu skupinu;
R2, R3 i R4, koji mogu biti isti ili različiti, i nalaze se na bilo kojem od dostupnih položaja u fenilnoj jezgri, neovisno predstavljaju atom vodika, atom halogena, CN, OH, (C1-6)alkilnu skupinu, izborno supstituiranu s atomom halogena ili OH; perhalogen(C1-3)alkil, (C1-6)alkoksi, perhalogen(C1-3)alkoksi, aminokarbonil, (C1-6)alkilaminokarbonil, di(C1-6)alkilaminokarbonil, aril, ariloksi; heteroaril; gdje arilna, ariloksi ili heteroarilna skupina mogu biti izborno supstituirane s atomom halogena, CN, OH ili (C1-6)alkilnom, perhalogen(C1-3)alkilnom ili (C1-6)alkoksi skupinom; gdje se podrazumijeva da najmanje jedan između R2, R3 i R4 nije H, te da arilna, ariloksi ili heteroarilna skupina mogu biti izborno supstituirane s atomom halogena, CN, OH ili (C1-6)alkilnom, perhalogen(C1-3)alkilnom ili (C1-6)alkoksi skupinom;
R5 predstavlja (C1-6)alkilnu ili (C2-6)alkenilnu skupinu; i
n predstavlja 1 ili 2;
u obliku baze ili adicijske soli s kiselinom;
izuzevši 5-klor-3-(2-klorfenil)-1,3-dihidro-3-[2-(4-metilpiperazin-1-il)acetamido]indol-2-on.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time što, u općoj formuli (I):
[image]
predstavlja jednostruku ili dvostruku vezu;
X predstavlja -CH<, -N< ili
[image]
;
Y predstavlja >N- ili >CH-, gdje se podrazumijeva da najmanje jedan između X i Y predstavlja N;
Ar predstavlja aril ili heteroarilna skupina, izborno supstituirana s jednim ili više supstituenata, koji mogu biti isti ili različiti i bira ih se između atoma halogena i (C1-6)alkil, perhalogen(C1-3)alkil, (C1-6)alkoksi i arilne skupine;
R1 predstavlja atom vodika ili -C(=O)(C1-6)alkil, -C(=O)aril ili (C1-6) alkilna skupina;
R2, R3 i R4, koji mogu biti isti ili različiti, i nalaze se na bilo kojem od dostupnih položaja u fenilnoj jezgri, neovisno predstavljaju atom vodika, atom halogena, (C1-6)alkilnu, perhalogen(C1-3)alkilnu, CN, arilnu, heteroarilnu, OH, (C1-6)alkoksi, perhalogen(C1-3)alkoksi, aminokarbonilnu, (C1-6)alkilaminokarbonilnu ili di(C1-6)alkilaminokarbonilna skupinu, gdje se podrazumijeva da najmanje jedan između R2, R3 i R4 nije H;
R5 predstavlja (C1-6)alkilnu skupinu;
n predstavlja 1 ili 2;
u obliku baze ili adicijske soli s kiselinom.
3. Spoj u skladu s patentnim zahtjevom 1 ili 2, naznačen time što, u općoj formuli (I):
[image]
predstavlja jednostruku ili dvostruku vezu;
X predstavlja -N<, -CH< ili
[image]
;
Y predstavlja >N- ili >CH-;
gdje se podrazumijeva da najmanje jedan između X i Y predstavlja N;
Ar predstavlja arilnu skupinu, izborno supstituiranu s jednim ili više supstituenata, koje se bira između atoma halogena i (C1-6)alkoksi, (C1-6)alkilnih, arilnih, trifluormetilnih i trifluormetoksi skupina;
R1 predstavlja atom vodika ili -C(=O)(C1-6)alkilnu, -C(=O)arilnu ili (C1-6)alkilnu skupinu;
R2, R3 i R4, koji mogu biti isti ili različiti, i nalaze se na bilo kojem od dostupnih položaja u fenilnoj jezgri, neovisno predstavljaju atom vodika, atom halogena, ili (C1-6)alkilnu ili trifluormetilnu skupinu, gdje se podrazumijeva da najmanje jedan između R2, R3 i R4 nije H;
R5 predstavlja (C1-6)alkilnu skupinu;
n predstavlja 1 ili 2;
u obliku baze ili adicijske soli s kiselinom.
4. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što, u općoj formuli (I):
[image]
predstavlja jednostruku ili dvostruku vezu;
X predstavlja -N<, -CH< ili
[image]
;
Y predstavlja >N- ili >CH-; gdje se podrazumijeva da najmanje jedan između X i Y predstavlja N;
Ar predstavlja fenilnu ili naftilnu skupinu, izborno supstituiranu s jednim ili više supstituenata, koje se bira između atoma halogena i metoksi, metilnih, tert-butilnih, fenilnih, trifluormetilnih i trifluormetoksi skupina;
R1 predstavlja atom vodika ili -C(=O)metilnu, -C(=O)fenilnu ili metilnu skupinu;
R2, R3 i R4, koji mogu biti isti ili različiti, i nalaze se na bilo kojem od dostupnih položaja u fenilnoj jezgri, neovisno predstavljaju atom vodika, atom halogena ili trifluormetilnu skupinu, gdje se podrazumijeva da najmanje jedan između R2, R3 i R4 nije H;
R5 predstavlja metil, etil ili 2-propilna skupina;
n predstavlja 1 ili 2;
u obliku baze ili adicijske soli s kiselinom.
5. Spoj u skladu s patentnim zahtjevom 1 ili 2, naznačen time što, u općoj formuli (I):
Ar predstavlja heteroarilnu skupinu, izborno supstituiranu s jednim ili više supstituenata, koji mogu biti isti ili različiti i bira ih se između atoma halogena i (C1-6)alkoksi, arilnih, perhalogen(C1-3)alkilnih i (C1-6)alkilnih skupina.
6. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što ga se bira između sljedećih spojeva:
(+)-N-[5,6-diklor-3-(4-klorfenil)-2-okso-2,3-dihidro-1H-indol-3-il]-2-(4-metilpiperazin-1-il)acetamida
(+)-N-[4,6-diklor-3-(4-trifluormetilfenil)-2-okso-2,3-dihidro-1H-indol-3-il]-2-(1-etilpiperid-4-il)acetamida
N-[4,6-diklor-3-(4-klorfenil)-2-okso-2,3-dihidro-1H-indol-3-il]-2-(4-metilpiperazin-1-il)acetamida
N-[4-trifluormetil-6-cijano-3-(4-klorfenil)-2-okso-2,3-dihidro-1H-indol-3-il]-2-(4-etilpiperazin-1-il)acetamida
(+)-N-[1-benzoil-5,6-diklor-3-(4-klorfenil)-2-okso-2,3-dihidro-1H-indol-3-il]-2-(4-metilpiperazin-1-il)acetamida
3-(4-klorfenil)-3-[2-(4-etilpiperazin-1-il)acetilamino]-2-okso-4-trifluormetil-2,3-dihidro-1H-indol-6-karboksamida
N-[6-klor-3-(4-klorfenil)-1,5-dimetil-2-okso-2,3-dihidro-1H-indol-3-il]-2-(4-metilpiperazin-1-il)acetamida
(+)-N-[4,6-diklor-3-(4-trifluormetilfenil)-2-okso-2,3-dihidro-1H-indol-3-il]-2-(1-etil-1,2,3,6-tetrahidropirid-4-il)acetamida
N-[4,6-diklor-3-(3,4-diklorfenil)-2-okso-2,3-dihidro-1H-indol-3-il]-2-(4-etilpiperazin-1-il)acetamida
N-[4,6-diklor-3-(3-fluor-4-klorfenil)-2-okso-2,3-dihidro-1H-indol-3-il]-2-(4-etilpiperazin-1-il)acetamida
N-[4,6-diklor-3-(3-trifluormetil-4-klorfenil)-2-okso-2,3-dihidro-1H-indol-3-il]-2-(4-etilpiperazin-1-il)acetamida
N-[4,6-diklor-1-etil-3-(2-metilbenzo[b]tiofen-5-il)-2-okso-2,3-dihidro-1H-indol-3-il]-2-(1-etilpiperid-4-il)acetamida
N-[4,6-diklor-1-etil-3-(2-metil-5-benzofuril)-2-okso-2,3-dihidro-1H-indol-3-il]-2-(4-etilpiperazin-1-il)acetamida
N-[4,6-diklor-3-(4-trifluormetoksifenil)-2-okso-2,3-dihidro-1H-indol-3-il]-2-(4-etilpiperazin-1-il)acetamida
u obliku baze ili adicijske soli s kiselinom.
7. Postupak dobivanja spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 6, naznačen time što uključuje korak koji se sastoji u reakciji spoja opće formule (V):
[image]
u kojoj su R2, R3, R4 i Ar definirani u skladu s bilo kojim od patentnih zahtjeva 1 do 6.
8. Postupak u skladu s patentnim zahtjevom 7, naznačen time što uključuje korake koji se sastoje u:
– reakciji navedenog spoja opće formule (V) sa spojem opće formule (VI):
[image]
u kojoj Hal' i Hal'', koji mogu biti isti ili različiti, neovisno predstavljaju atom halogena;
– zatim u reakciji dobivenog spoja opće formule (III)
[image]
sa spojem opće formule (IV):
[image]
u kojoj su R2, R3, R4, R5, Y, Ar i n definirani kao u općoj formuli (I), a Hal'' predstavlja atom halogena;
– gdje izborno slijedi korak koji se sastoji u reakciji dobivenog produkta formule (I), u kojoj X predstavlja -N<, a R1 je H, sa spojem formule (II):
R1-Hal (II)
u kojoj R1, koji nije H, je definiran kao u općoj formuli (I), a Hal predstavlja atom halogena.
9. Postupak u skladu s patentnim zahtjevom 7, naznačen time što uključuje korak koji se sastoji u reakciji navedenog spoja opće formule (V) sa spojem opće formule (VIII):
[image]
u kojoj
[image]
,
X, Y, R5 i n su definirani u skladu s bilo kojim od patentnih zahtjeva 1 do 6;
gdje izborno slijedi korak koji se sastoji u reakciji dobivenog produkta formule (I), u kojoj R1 je H, sa spojem formule (II):
R1-Hal (II)
u kojoj R1, koji nije H, je definiran kao u općoj formuli (I), a Hal predstavlja atom halogena.
10. Postupak dobivanja spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 6, naznačen time što uključuje korak koji se sastoji u reakciji spoja opće formule (XXVIII):
[image]
u kojoj su R2, R3, R4 i Ar definirani u skladu s bilo kojim od patentnih zahtjeva 1 do 6, a ALK predstavlja alkilnu skupinu.
11. Postupak u skladu s patentnim zahtjevom 10, naznačen time što uključuje korake koji se sastoje u
– reakciji navedenog spoja opće formule (XXVIII) sa spojem opće formule (VI):
[image]
u kojoj Hal' i Hal'', koji mogu biti isti ili različiti, neovisno predstavljaju atom halogena;
– zatim u reakciji dobivenog spoja opće formule (XXIX)
[image]
sa spojem opće formule (IV):
[image]
u kojoj su R2, R3, R4, R5, Y, Ar i n definirani kao u općoj formuli (I), a Hal" predstavlja atom halogena.
12. Postupak u skladu s patentnim zahtjevom 10, naznačen time što uključuje korak koji se sastoji u reakciji navedenog spoja opće formule (XXVIII) sa spojem opće formule (VII):
[image]
u kojoj
[image]
,
X, Y, R5 i n su definirani u skladu s bilo kojim od patentnih zahtjeva 1 do 6.
13. Postupak u skladu s bilo kojim od patentnih zahtjeva 7 do 12, naznačen time što uključuje dodatni korak, koji se sastoji u izdvajanju željenog spoja opće formule (I).
14. Spoj formule (III):
[image]
naznačen time što R2, R3, R4 i Ar su definirani u skladu s bilo kojim od patentnih zahtjeva 1 do 6, a Hal predstavlja atom halogena, izuzevši 5-klor-3-(2-kloracetamido)-3-(2-klorfenil)-1,3-dihidroindol-2-on.
15. Spoj formule (III) u skladu s patentnim zahtjevom 14, naznačen time što:
Ar predstavlja heteroarilnu skupinu, izborno supstituiranu s jednim ili više supstituenata, koji mogu biti isti ili različiti i bira ih se između atoma halogena i (C1-6)alkoksi, arilnih, perhalogen(C1-3)alkilnih i (C1-6)alkilnih skupina.
16. Spoj opće formule (XXVIII):
[image]
naznačen time što R2, R3, R4 i Ar su definirani u skladu s bilo kojim od patentnih zahtjeva 1 do 6, a ALK predstavlja alkilnu skupinu.
17. Spoj opće formule (XXIX):
[image]
naznačen time što R2, R3, R4 i Ar su definirani u skladu s bilo kojim od patentnih zahtjeva 1 do 6, ALK predstavlja alkilnu skupinu, a Hal'' predstavlja atom halogena.
18. Medikament, naznačen time što sadrži spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 6, ili adicijsku sol tog spoja s farmaceutski prihvatljivom kiselinom.
19. Farmaceutski pripravak, naznačen time što sadrži spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 6, ili farmaceutski prihvatljivu sol.
20. Upotreba spoja u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačena time što je navedeni lijek namijenjen pripravi medikamenta za sprječavanje ili liječenje pretilosti, dijabetesa, poremećaja apetita i prekomjerne tjelesne težine.
21. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 6, naznačen time što je namijenjen sprječavanju ili liječenju pretilosti, dijabetesa, poremećaja apetita i prekomjerne tjelesne težine.
22. Kombinacija, naznačena time što sadrži jedan ili više spojeva u skladu s bilo kojim od patentnih zahtjeva 1 do 6 s jednim ili više aktivnih sastojaka.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0705858A FR2920023B1 (fr) | 2007-08-16 | 2007-08-16 | Derives de l'indol-2-one disubstitues en 3, leur preparation et leur application en therapeutique |
| PCT/FR2008/001190 WO2009056707A2 (fr) | 2007-08-16 | 2008-08-14 | Dérivés de l'ind0l-2-0ne disubstitues en 3, leur preparation et leur application en thérapeutique |
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| HRP20120466T1 true HRP20120466T1 (hr) | 2012-07-31 |
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| PE20090938A1 (es) | 2007-08-16 | 2009-08-08 | Boehringer Ingelheim Int | Composicion farmaceutica que comprende un derivado de benceno sustituido con glucopiranosilo |
| FR2941946B1 (fr) * | 2009-02-12 | 2011-03-25 | Sanofi Aventis | Derives de 3-benzofuranyl-indol-2-one-3-acetamidopiperazines substitues, leur preparation et leur application en therapeutique |
| FR2941947B1 (fr) * | 2009-02-12 | 2011-03-25 | Sanofi Aventis | Derives de 3-benzofuranyl-indol-2-one subtitues en 3, leur preparation et leur application en therapeutique |
| PT2395983T (pt) | 2009-02-13 | 2020-07-03 | Boehringer Ingelheim Int | Composição farmacêutica compreendendo um inibidor de sglt2, um inibidor de dp-iv e opcionalmente um agente antidiabético adicional e suas utilizações |
| UY33937A (es) | 2011-03-07 | 2012-09-28 | Boehringer Ingelheim Int | Composiciones farmacéuticas que contienen inhibidores de dpp-4 y/o sglt-2 y metformina |
| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| US9555001B2 (en) | 2012-03-07 | 2017-01-31 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition and uses thereof |
| CN108658836B (zh) * | 2018-05-15 | 2021-04-20 | 宁波大学 | 一种3-取代-3-叠氮基吲哚-2-酮类化合物的制备方法 |
| EP3912625A1 (en) * | 2020-05-20 | 2021-11-24 | Kaerus Bioscience Limited | Novel maxi-k potassium channel openers for the treatment of fragile x associated disorders |
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| FR2714378B1 (fr) * | 1993-12-24 | 1996-03-15 | Sanofi Sa | Dérivés de l'indol-2-one substitués en 3 par un groupe azoté, leur préparation, les compositions pharmaceutiques en contenant. |
| KR100680085B1 (ko) * | 1998-08-20 | 2007-02-28 | 다이닛본 스미토모 세이야꾸 가부시끼가이샤 | 성장호르몬 방출촉진제로서 옥신돌 유도체 |
| FR2827604B1 (fr) * | 2001-07-17 | 2003-09-19 | Sanofi Synthelabo | Nouveaux derives de 1-phenylsulfonyl-1,3-dihydro-2h-indol-2- one, un procede pour leur preparation et les compositions pharmaceutiques en contenant |
| JPWO2005035498A1 (ja) * | 2003-10-08 | 2006-12-21 | 住友製薬株式会社 | 含窒素二環性化合物の摂食調節剤としての用途 |
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2007
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2008
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- 2008-08-14 MX MX2010001851A patent/MX2010001851A/es active IP Right Grant
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