HRP20090504T1 - 3-(((4-fenil)-piperazin-1-il)-alkil)-3-alkil-1,3-dihidro-2h-indol-2-on derivati i srodni spojevi za tretiranje poremećaja središnjeg živčanog sustava - Google Patents
3-(((4-fenil)-piperazin-1-il)-alkil)-3-alkil-1,3-dihidro-2h-indol-2-on derivati i srodni spojevi za tretiranje poremećaja središnjeg živčanog sustava Download PDFInfo
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- HRP20090504T1 HRP20090504T1 HR20090504T HRP20090504T HRP20090504T1 HR P20090504 T1 HRP20090504 T1 HR P20090504T1 HR 20090504 T HR20090504 T HR 20090504T HR P20090504 T HRP20090504 T HR P20090504T HR P20090504 T1 HRP20090504 T1 HR P20090504T1
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- -1 (4-phenyl)-piperazin-1-yl Chemical group 0.000 title claims abstract 4
- 150000001875 compounds Chemical class 0.000 title claims 20
- 238000011282 treatment Methods 0.000 title claims 4
- 208000015114 central nervous system disease Diseases 0.000 title claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 9
- 239000001257 hydrogen Substances 0.000 claims abstract 9
- 150000003839 salts Chemical class 0.000 claims abstract 9
- 239000002253 acid Substances 0.000 claims abstract 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract 6
- 150000002367 halogens Chemical class 0.000 claims abstract 6
- 150000002431 hydrogen Chemical class 0.000 claims abstract 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract 2
- 150000005625 indol-2-ones Chemical class 0.000 claims abstract 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 2
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 5
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims 3
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 3
- 208000036626 Mental retardation Diseases 0.000 claims 3
- 208000019022 Mood disease Diseases 0.000 claims 3
- 208000001647 Renal Insufficiency Diseases 0.000 claims 3
- 208000006011 Stroke Diseases 0.000 claims 3
- 208000009205 Tinnitus Diseases 0.000 claims 3
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 3
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 3
- 210000003169 central nervous system Anatomy 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 201000006370 kidney failure Diseases 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 238000002360 preparation method Methods 0.000 claims 3
- 238000011321 prophylaxis Methods 0.000 claims 3
- 208000020016 psychiatric disease Diseases 0.000 claims 3
- 201000000980 schizophrenia Diseases 0.000 claims 3
- 231100000886 tinnitus Toxicity 0.000 claims 3
- MMROWWMGPGURGC-UHFFFAOYSA-N 3-[4-[4-(3-chlorophenyl)piperazin-1-yl]butyl]-3-ethyl-2-oxo-1h-indole-5-sulfonamide Chemical compound O=C1NC2=CC=C(S(N)(=O)=O)C=C2C1(CC)CCCCN(CC1)CCN1C1=CC=CC(Cl)=C1 MMROWWMGPGURGC-UHFFFAOYSA-N 0.000 claims 2
- OGUHCHBFMUYJMX-UHFFFAOYSA-N 3-[4-[4-(3-chlorophenyl)piperazin-1-yl]butyl]-3-ethyl-5-fluoro-1h-indol-2-one Chemical compound O=C1NC2=CC=C(F)C=C2C1(CC)CCCCN(CC1)CCN1C1=CC=CC(Cl)=C1 OGUHCHBFMUYJMX-UHFFFAOYSA-N 0.000 claims 2
- ZXFXIIYDRJKCMJ-UHFFFAOYSA-N 3-[4-[4-(4-chlorophenyl)piperazin-1-yl]butyl]-3-ethyl-1h-indol-2-one Chemical compound O=C1NC2=CC=CC=C2C1(CC)CCCCN(CC1)CCN1C1=CC=C(Cl)C=C1 ZXFXIIYDRJKCMJ-UHFFFAOYSA-N 0.000 claims 2
- ISWLMFBTCIVZDN-UHFFFAOYSA-N 3-[4-[4-(4-chlorophenyl)piperazin-1-yl]butyl]-3-ethyl-5-fluoro-1h-indol-2-one Chemical compound O=C1NC2=CC=C(F)C=C2C1(CC)CCCCN(CC1)CCN1C1=CC=C(Cl)C=C1 ISWLMFBTCIVZDN-UHFFFAOYSA-N 0.000 claims 2
- IIMFJUUIXYQSJE-UHFFFAOYSA-N 5-chloro-3-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-3-ethyl-1h-indol-2-one Chemical compound O=C1NC2=CC=C(Cl)C=C2C1(CC)CCCN(CC1)CCN1C1=CC=CC(Cl)=C1 IIMFJUUIXYQSJE-UHFFFAOYSA-N 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 2
- 230000030833 cell death Effects 0.000 claims 2
- 150000007522 mineralic acids Chemical class 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- LJGCNYCNHDTRSH-UHFFFAOYSA-N 3-[4-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]butyl]-3-ethyl-1h-indol-2-one Chemical compound O=C1NC2=CC=CC=C2C1(CC)CCCCN1CCN(C=2C=3OCCOC=3C=CC=2)CC1 LJGCNYCNHDTRSH-UHFFFAOYSA-N 0.000 claims 1
- QOLSSOMCERQWLI-UHFFFAOYSA-N 3-ethyl-3-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]-1h-indol-2-one Chemical compound O=C1NC2=CC=CC=C2C1(CC)CCCCN(CC1)CCN1C1=CC=CC=C1OC QOLSSOMCERQWLI-UHFFFAOYSA-N 0.000 claims 1
- FKRVQPWZHRSDKZ-UHFFFAOYSA-N 5,7-dichloro-3-[4-[4-(4-chlorophenyl)piperazin-1-yl]butyl]-3-methyl-1h-indol-2-one Chemical compound O=C1NC(C(=CC(Cl)=C2)Cl)=C2C1(C)CCCCN(CC1)CCN1C1=CC=C(Cl)C=C1 FKRVQPWZHRSDKZ-UHFFFAOYSA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 206010026749 Mania Diseases 0.000 claims 1
- 206010041250 Social phobia Diseases 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- NOWFIMHNXPZVSK-UHFFFAOYSA-N egis-12,233 Chemical compound O=C1NC(C(=CC(Cl)=C2)Cl)=C2C1(CC)CCCCN(CC1)CCN1C1=CC=C(Cl)C=C1 NOWFIMHNXPZVSK-UHFFFAOYSA-N 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000026030 halogenation Effects 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 claims 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 150000004885 piperazines Chemical class 0.000 claims 1
Classifications
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- 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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- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/4045—Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
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Abstract
Derivati 3, 3-dialkil indol-2-ona opće formule (I), ,naznačeni time, daR1 označuje vodik, halogen, alkil koji ima 1-7 atoma ugljika ili sulfonamido; R2 označuje vodik ili halogen; R3 označuje vodik, R4 označuje etil ili 2-metil-propil; R5 označuje skupinu opće formule, gdje Q označuje dušik, a W označuje CH; R6, R7 i R8 svaki označuje vodik, halogen, trifluormetil, alkil ili alkoksi koji ima 1-7 atoma ugljika, ili R6 i R7 zajedno označuju etilendioksi, m je jednako 0, l, ili 2; a je jednostruka, dvostruka ili trostruka veza: te njihove farmaceutski prihvatljive kisele adicijske soli. Patent sadrži još 8 patentnih zahtjeva.
Claims (9)
1. Derivati 3, 3-dialkil indol-2-ona opće formule (I),
[image]
,
naznačeni time, da
R1 označuje vodik, halogen, alkil koji ima 1-7 atoma ugljika ili sulfonamido;
R2 označuje vodik ili halogen;
R3 označuje vodik,
R4 označuje etil ili 2-metil-propil;
R5 označuje skupinu opće formule,
[image]
gdje Q označuje dušik, a W označuje CH;
R6, R7 i R8 svaki označuje vodik, halogen, trifluormetil, alkil ili alkoksi koji ima 1-7 atoma ugljika, ili R6 i R7 zajedno označuju etilendioksi,
m je jednako 0, l, ili 2;
a je jednostruka, dvostruka ili trostruka veza:
te njihove farmaceutski prihvatljive kisele adicijske soli.
2. Spoj prema patentnom zahtjevu 1, naznačen time što odabran iz sljedećeg skupa:
5-klor-3-{3-[4-(3-klorfenil)-piperazin-1-il]-propil}-3-etil-1,3-dihidro-2H-indol-2-on,
3-{4-[4-(3-klorfenil)-piperazin-1-il]-butil}-3-etil-5-fluor-1,3-dihidro-2H-indol-2-on,
5,7-diklor-3-{4-[4-(4-klorfenil)-piperazin-1-il]-butil}-3-etil-1,3-dihidro-2H-indol-2-on,
3-{4-[4-(4-klorfenil)-piperazin-1-il]-butil}-3-etil-1,3-dihidro-2H-indol-2-on,
3-{4-[4-(4-klorfenil)-piperazin-1-il]-butil}-3-etil-5-fluor-1,3-dihidro-2H-indol-2-on,
3-{4-[4-(3-klorfenil)-piperazin-1-il]-butil}-3-etil-1,3-dihidro-2H-indol-2-on-5-sulfonamid,
3-{4-[4-(2, 3-dihidrobenzo[l, 4]dioksin-5-il)-piperazin-1-il]-butil}-3-etil-1,3-dihidro-2H-indol-2-on,
3-{4-[4-(2, 3-dihidrobenzo[l, 4]dioksin-5-il)-piparazin-1-il]-butil}-3-izobutil-1,3-dihidro-2H-indol-2-on,
3-etil-3-{4-[4-(2-metoksifenil)-piperazin-1-il]-butil}-1,3-dihidro-2H-indol-2-on,
te njegove farmaceutski prihvatljive kisele adicijske soli.
3. Farmaceutske smjese, naznačene time što kao aktivan sastojak sadrže bar jedan spoj opće formule (I) sukladno zahtjevu 1 ili 2 ili njegovu farmaceutski prihvatljivu kiselu adicijsku sol u smjesi s jednim ili više odgovarajućih nosača ili pomoćnih sredstava.
4. Farmaceutske smjese prema zahtjevu 3, naznačene time što su korisne u tretiranju ili profilaksi poremećaja središnjeg živčanog sustava, osobito depresije, shizofrenije, poremećaja raspoloženja, straha od društva, duševnih poremećaja, moždanog udara, maloumnosti, staničnog odumiranja u određenim dijelovima središnjeg živčanog sustava, Alzheimerove bolesti, stresa, gastrointestinalnih bolesti, kardiovaskularnih bolesti, renalne insuficijencije, tinitusa ili bradiakuzije.
5. Farmaceutske smjese sukladne zahtjevu 3 ili 4, naznačene time što kao aktivan sastojak sadrže 5-klor-3-{3-[4-(3-klorfenil)-piperazin-1-il]-propil}-3-etil-1,3-dihidro-2H-indol-2-on, 3-{4-[4-(3-klorfenil)-piperazin-1-il]-butil}-3-etil-5-fluor-1,3-dihidro-2H-indol-2-on, 5,7-diklor-3-{4-[4-(4-klorfenil)-piperazin-1-il]-butil}-3-metil-1,3-dihidro-2H-indol-2-on, 3-{4-[4-(4-klorfenil)-piperazin-1-il]-butil}-3-etil-1,3-dihidro-2H-indol-2-on, 3-{4-[4-(4-klorfenil)-piperazin-1-il]-butil}-3-etil-5-fluor-1,3-dihidro-2H-indol-2-on, 3-{4-[4-(3-klorfenil)-piperazin-1-il]-butil}-3-etil-1,3-dihidro-2H-indol-2-on-5-sulfonamid, 3-{4-[4-(2, 3-dihidrobenzo[l,4]dioksin-5-il)-piperazin-1-il]-butil}-3-etil-1,3-dihidro-2H-indol-2-on, 3-{4-[4-(2,3-dihidrobenzo[l,4]dioxin-5-il)-piperazin-1-il]-butil}-3-metoksifenil)-piperazin-1-il]-butil}-1,3-dihidro-2H-indol-2-on ili njegove farmaceutski prihvatljive kisele adicijske soli u smjesi s jednim ili više pogodnih nosača ili pomoćnih sredstava.
6. Postupak za priređivanje spoja kao što je definirano u patentnom zahtjevu 1, naznačen time što obuhvaća:
(a) reakciju spoja opće formule (III),
[image]
gdje su R1, R2, R3, R4, m i a kao što je navedeno prije i L je klor, brom ili hidroksi ili alkilsulfoniloksi ili arilsulfoniloksi skupina, s piperazinskim derivatom opće formule (IV),
[image]
gdje je R5 kao što je navedeno prije,
u prisutnosti kiselog vezujućeg sredstva; ili
(b) reakciju spoja opće formule (VI),
[image]
gdje su R1, R2, R3 i R4 kao što je navedeno prije, sa spojem opće formule (VII),
[image]
gdje je m kao što je navedeno prije, dok a označuje jednostruku, dvostruku ili trostruku vezu i L je klor, brom ili hidroksi ili alkilsulfoniloksi ili arilsulfoniloksi skupina, u prisutnosti jake baze;
(c) za priređivanje spojeva opće formule (I), gdje je n jednako 1 i a označuje trostruku vezu, reakciju spoja opće formule (VIII),
[image]
gdje su R1, R2, R3, R4 i m su kao što je prije navedeno, s formaldehidom, proizvoljno prevođenje tako dobivenog spoja opće formule (III), gdje L označuje hidroksilnu skupinu, u spoj opće formule (III), gdje je L atom halogena ili arilsulfoniloksi ili alkilsulfoniloksi skupina, te reakcija tako dobivenog spoja opće formule (III), gdje je a trostruka veza i n je jednako 1, sa spojem opće formule (IV) u prisutnosti jake baze; ili
(d) za priređivanje spojeva opće formule (I), gdje su R1, R2, R3, R4, R5 i m kao što je navedeno prije i a označuje jednostruku ili dvostruku vezu, podvrgavanje odgovarajućeg spoja opće formule (I), gdje a označuje trostruku vezu, redukciji; ili
(e) za priređivanje spojeva opće formule (I), gdje su R1, R2, R3, R4, R5 i m kao što je navedeno prije i a označuje jednostruku vezu, podvrgavanje odgovarajućeg spoja opće formule (I), gdje a označuje dvostruku ili trostruku vezu, redukciji, te, ako se želi, halogeniranje produkta koji sadrži vodik na mjestu R2, ili oslobađanje slobodne baze iz njenih soli ili njeno prevođenje u farmaceutski prihvatljivu kiselu adicijsku sol s organskom ili anorganskom kiselinom.
7. Upotreba spojeva formule (I) prema bilo kojem zahtjevu 1 ili 2, za proizvodnju medikamenta.
8. Upotreba barem jednog spoja prema zahtjevu 1 ili 2 opće formule (I) ili njegove farmaceutski prihvatljive organske ili anorganske kisele adicijske soli za pripravu farmaceutskog pripravka za tretiranje ili profilaksu poremećaja središnjeg živčanog sustava, osobito depresije, shizofrenije, poremećaja raspoloženja, straha od društva, duševnih poremećaja, moždanog udara, maloumnosti, staničnog odumiranja u određenim dijelovima središnjeg živčanog sustava, Alzheimerove bolesti, stresa, gastrointestinalnih bolesti, kardiovaskularnih bolesti, renalne insuficijencije, tinitusa ili bradiakuzije.
9. Postupak proizvodnje farmaceutskog pripravka koji je pogodan za tretiranje ili profilaksu poremećaja središnjeg živčanog sustava, osobito depresije, tjeskobe, shizofrenije, poremećaja raspoloženja, straha od društva, manije, duševnog poremećaja, moždanog udara, maloumnosti, Alzheimerove bolesti, stresa, gastrointestinalnih poremećaja, kardiovaskularnih bolesti, renalne insuficijencije, tinitusa ili bradiakuzije, naznačen time što obuhvaća miješanje bar jednog spoja opće formule (I) prema bilo kojem zahtjevu od 1 do 12 ili njegove farmaceutski prihvatljive kisele adicijske soli s farmaceutskim nosačem i proizvoljno drugim pomoćnim sredstvom te prevođenje smjese u galenski oblik.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0400957A HU0400957D0 (en) | 2004-05-11 | 2004-05-11 | Piperazinbe derivatives of dialkyl oxindoles |
| HU0500464A HUP0500464A3 (en) | 2005-05-05 | 2005-05-05 | Piperazine derivatives of dialkyl-oxindoles |
| PCT/HU2005/000052 WO2005109987A2 (en) | 2004-05-11 | 2005-05-11 | 3-(((4-phenyl)-piperazine-1-yl)-alkyl)-3-alkyl-1, 3-dihydro-2h-indol-2-one derivatives and related compounds for the treatment of central nervous system disorders |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20090504T1 true HRP20090504T1 (hr) | 2009-10-31 |
Family
ID=89986001
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20060404A HRP20060404A2 (hr) | 2004-05-11 | 2006-11-20 | 3-(((4-fenil)-piperazin-1-il)-alkil)-3-alkil-1,3-dihidro-2h-indol-2-on derivati i srodni spojevi zatretiranje poremećaja središnjeg živčanog sustava |
| HR20090504T HRP20090504T1 (hr) | 2004-05-11 | 2009-09-22 | 3-(((4-fenil)-piperazin-1-il)-alkil)-3-alkil-1,3-dihidro-2h-indol-2-on derivati i srodni spojevi za tretiranje poremećaja središnjeg živčanog sustava |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20060404A HRP20060404A2 (hr) | 2004-05-11 | 2006-11-20 | 3-(((4-fenil)-piperazin-1-il)-alkil)-3-alkil-1,3-dihidro-2h-indol-2-on derivati i srodni spojevi zatretiranje poremećaja središnjeg živčanog sustava |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US7786129B2 (hr) |
| EP (1) | EP1776339B1 (hr) |
| JP (1) | JP2007537229A (hr) |
| KR (1) | KR20070011594A (hr) |
| AT (1) | ATE435204T1 (hr) |
| AU (1) | AU2005244389B2 (hr) |
| BG (1) | BG109771A (hr) |
| CA (1) | CA2565514A1 (hr) |
| CZ (1) | CZ2006777A3 (hr) |
| DE (1) | DE602005015223D1 (hr) |
| DK (1) | DK1776339T3 (hr) |
| EA (1) | EA014236B1 (hr) |
| ES (1) | ES2329388T3 (hr) |
| HR (2) | HRP20060404A2 (hr) |
| IL (1) | IL179029A (hr) |
| MX (1) | MXPA06013069A (hr) |
| NO (1) | NO20065659L (hr) |
| NZ (1) | NZ551547A (hr) |
| PL (1) | PL1776339T3 (hr) |
| PT (1) | PT1776339E (hr) |
| RS (1) | RS20060623A (hr) |
| SI (1) | SI1776339T1 (hr) |
| SK (1) | SK51072006A3 (hr) |
| WO (1) | WO2005109987A2 (hr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5528699B2 (ja) | 2006-05-16 | 2014-06-25 | 武田薬品工業株式会社 | 縮合複素環化合物およびその用途 |
| EP2789338A3 (en) | 2007-11-15 | 2015-01-14 | Takeda Pharmaceutical Company Limited | Condensed pyridine derivate and use thereof |
| HUP0900071A2 (en) * | 2009-02-06 | 2010-10-28 | Egis Gyogyszergyar Nyilvanosan | Optically active 3-[(phenyl-piperazin-1-yl)alkyl]-3-alkyl-oxindole derivatives influencing the central nervous system and pharmaceutical compositions containing them |
| JPWO2019131902A1 (ja) | 2017-12-27 | 2020-12-10 | 武田薬品工業株式会社 | 腹圧性尿失禁および便失禁の治療薬 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2635104B1 (fr) | 1988-08-03 | 1992-04-30 | Synthelabo | Derives d'indolone, leur preparation et leur application en therapeutique |
| GB8830312D0 (en) * | 1988-12-28 | 1989-02-22 | Lundbeck & Co As H | Heterocyclic compounds |
| WO1998008816A1 (fr) | 1996-08-26 | 1998-03-05 | Meiji Seika Kaisha, Ltd. | Derives d'indoxyle et psychotropes |
| US20070232662A1 (en) | 2004-05-11 | 2007-10-04 | Egis Gyogyszergyar Rt. | Indol-2-One Derivatives for the Treatment of Central Nervous Disorders, Gastrointestinal Disorders and Cardiovascular Disorders |
| DK1751106T3 (da) * | 2004-05-11 | 2009-03-09 | Egis Gyogyszergyar Nyrt | Piperazinderivater af alkyloxindoler |
-
2005
- 2005-05-11 CZ CZ20060777A patent/CZ2006777A3/cs unknown
- 2005-05-11 US US11/596,473 patent/US7786129B2/en not_active Expired - Fee Related
- 2005-05-11 AU AU2005244389A patent/AU2005244389B2/en not_active Ceased
- 2005-05-11 WO PCT/HU2005/000052 patent/WO2005109987A2/en active Application Filing
- 2005-05-11 ES ES05779909T patent/ES2329388T3/es active Active
- 2005-05-11 RS RSP-2006/0623A patent/RS20060623A/sr unknown
- 2005-05-11 SI SI200530785T patent/SI1776339T1/sl unknown
- 2005-05-11 DE DE602005015223T patent/DE602005015223D1/de active Active
- 2005-05-11 PL PL05779909T patent/PL1776339T3/pl unknown
- 2005-05-11 JP JP2007512537A patent/JP2007537229A/ja not_active Ceased
- 2005-05-11 DK DK05779909T patent/DK1776339T3/da active
- 2005-05-11 MX MXPA06013069A patent/MXPA06013069A/es active IP Right Grant
- 2005-05-11 SK SK5107-2006A patent/SK51072006A3/sk not_active Application Discontinuation
- 2005-05-11 CA CA002565514A patent/CA2565514A1/en not_active Abandoned
- 2005-05-11 KR KR1020067026024A patent/KR20070011594A/ko not_active Application Discontinuation
- 2005-05-11 EA EA200602083A patent/EA014236B1/ru not_active IP Right Cessation
- 2005-05-11 EP EP05779909A patent/EP1776339B1/en active Active
- 2005-05-11 NZ NZ551547A patent/NZ551547A/en unknown
- 2005-05-11 PT PT05779909T patent/PT1776339E/pt unknown
- 2005-05-11 AT AT05779909T patent/ATE435204T1/de active
-
2006
- 2006-11-02 IL IL179029A patent/IL179029A/en not_active IP Right Cessation
- 2006-11-20 HR HR20060404A patent/HRP20060404A2/hr not_active Application Discontinuation
- 2006-12-06 NO NO20065659A patent/NO20065659L/no not_active Application Discontinuation
- 2006-12-11 BG BG109771A patent/BG109771A/bg unknown
-
2009
- 2009-09-22 HR HR20090504T patent/HRP20090504T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL1776339T3 (pl) | 2009-12-31 |
| WO2005109987A9 (en) | 2007-03-29 |
| ATE435204T1 (de) | 2009-07-15 |
| IL179029A0 (en) | 2007-03-08 |
| BG109771A (bg) | 2008-05-30 |
| RS20060623A (en) | 2008-09-29 |
| US20070232619A1 (en) | 2007-10-04 |
| DK1776339T3 (da) | 2009-11-02 |
| AU2005244389A1 (en) | 2005-11-24 |
| EA014236B1 (ru) | 2010-10-29 |
| JP2007537229A (ja) | 2007-12-20 |
| EP1776339B1 (en) | 2009-07-01 |
| EA200602083A1 (ru) | 2007-06-29 |
| HRP20060404A2 (hr) | 2007-04-30 |
| WO2005109987A3 (en) | 2006-05-04 |
| IL179029A (en) | 2011-11-30 |
| SI1776339T1 (sl) | 2009-12-31 |
| NZ551547A (en) | 2010-06-25 |
| ES2329388T3 (es) | 2009-11-25 |
| CZ2006777A3 (cs) | 2007-03-14 |
| DE602005015223D1 (de) | 2009-08-13 |
| AU2005244389B2 (en) | 2011-09-01 |
| CA2565514A1 (en) | 2005-11-24 |
| PT1776339E (pt) | 2009-09-16 |
| WO2005109987A2 (en) | 2005-11-24 |
| MXPA06013069A (es) | 2007-03-30 |
| KR20070011594A (ko) | 2007-01-24 |
| US7786129B2 (en) | 2010-08-31 |
| EP1776339A2 (en) | 2007-04-25 |
| NO20065659L (no) | 2007-01-29 |
| SK51072006A3 (sk) | 2007-05-03 |
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