DK3180001T3 - Aktiv metabolit af 1-[(2-bromphenyl)sulfonyl]-5-methoxy-3-[(4-methyl-1-piperazinyl)methyl]-1h-indol-dimesylat-monohydrat og dimesylat-dihydratsalt af aktivt metabolit - Google Patents
Aktiv metabolit af 1-[(2-bromphenyl)sulfonyl]-5-methoxy-3-[(4-methyl-1-piperazinyl)methyl]-1h-indol-dimesylat-monohydrat og dimesylat-dihydratsalt af aktivt metabolit Download PDFInfo
- Publication number
- DK3180001T3 DK3180001T3 DK14825443.6T DK14825443T DK3180001T3 DK 3180001 T3 DK3180001 T3 DK 3180001T3 DK 14825443 T DK14825443 T DK 14825443T DK 3180001 T3 DK3180001 T3 DK 3180001T3
- Authority
- DK
- Denmark
- Prior art keywords
- formula
- methyl
- methoxy
- indole
- sulfonyl
- Prior art date
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- XKDCUJBWVGDNSH-UHFFFAOYSA-N 1-(2-bromophenyl)sulfonyl-5-methoxy-3-[(4-methylpiperazin-1-yl)methyl]indole;methanesulfonic acid;hydrate Chemical class O.CS(O)(=O)=O.CS(O)(=O)=O.C12=CC(OC)=CC=C2N(S(=O)(=O)C=2C(=CC=CC=2)Br)C=C1CN1CCN(C)CC1 XKDCUJBWVGDNSH-UHFFFAOYSA-N 0.000 title claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 61
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 41
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 25
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 24
- MTGVOBSEOMBLDT-UHFFFAOYSA-N COC1=CC=C2N(C=C(CN3CCN(CC3)C(=O)OC(C)(C)C)C2=C1)S(=O)(=O)C1=C(Br)C=CC=C1 Chemical compound COC1=CC=C2N(C=C(CN3CCN(CC3)C(=O)OC(C)(C)C)C2=C1)S(=O)(=O)C1=C(Br)C=CC=C1 MTGVOBSEOMBLDT-UHFFFAOYSA-N 0.000 claims description 21
- KLWSFLZYJPOGSH-UHFFFAOYSA-N COC1=CC=C2NC=C(CN3CCN(CC3)C(=O)OC(C)(C)C)C2=C1 Chemical compound COC1=CC=C2NC=C(CN3CCN(CC3)C(=O)OC(C)(C)C)C2=C1 KLWSFLZYJPOGSH-UHFFFAOYSA-N 0.000 claims description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- OFZBXXDIKHYMDA-UHFFFAOYSA-N COC1=CC=C2N(C=C(CN3CCNCC3)C2=C1)S(=O)(=O)C1=C(Br)C=CC=C1 Chemical group COC1=CC=C2N(C=C(CN3CCNCC3)C2=C1)S(=O)(=O)C1=C(Br)C=CC=C1 OFZBXXDIKHYMDA-UHFFFAOYSA-N 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 208000024827 Alzheimer disease Diseases 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 238000000746 purification Methods 0.000 claims description 9
- VFPWGZNNRSQPBT-UHFFFAOYSA-N 2-bromobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1Br VFPWGZNNRSQPBT-UHFFFAOYSA-N 0.000 claims description 8
- -1 3 - [(1-butyloxycarbonyl-piperazin-4-yl) methyl] -5-methoxy-1H-indole Chemical compound 0.000 claims description 8
- 201000000980 schizophrenia Diseases 0.000 claims description 8
- ATRHOXITHDTKAU-UHFFFAOYSA-N CS(O)(=O)=O.CS(O)(=O)=O.COc1ccc2n(cc(CN3CCNCC3)c2c1)S(=O)(=O)c1ccccc1Br Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.COc1ccc2n(cc(CN3CCNCC3)c2c1)S(=O)(=O)c1ccccc1Br ATRHOXITHDTKAU-UHFFFAOYSA-N 0.000 claims description 7
- HEFIWZORGMNALZ-UHFFFAOYSA-N Cl.Cl.COc1ccc2n(cc(CN3CCNCC3)c2c1)S(=O)(=O)c1ccccc1Br Chemical compound Cl.Cl.COc1ccc2n(cc(CN3CCNCC3)c2c1)S(=O)(=O)c1ccccc1Br HEFIWZORGMNALZ-UHFFFAOYSA-N 0.000 claims description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 7
- HNTMIXBCJUGFQI-UHFFFAOYSA-N 1-(2-bromophenyl)sulfonyl-5-methoxy-3-(piperazin-1-ylmethyl)indole methanesulfonic acid dihydrate Chemical compound O.O.COc1ccc2c(c1)c(CN3CCNCC3)cn2S(=O)(=O)c4ccccc4Br.CS(=O)(=O)O.CS(=O)(=O)O HNTMIXBCJUGFQI-UHFFFAOYSA-N 0.000 claims description 6
- DWAQDRSOVMLGRQ-UHFFFAOYSA-N 5-methoxyindole Chemical compound COC1=CC=C2NC=CC2=C1 DWAQDRSOVMLGRQ-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 claims description 6
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- 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
- A61K31/4035—Isoindoles, e.g. phthalimide
-
- A—HUMAN NECESSITIES
- 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
-
- A—HUMAN NECESSITIES
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
-
- 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
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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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- 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
- C07D403/06—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 carbon chain containing only aliphatic carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (14)
1. Aktivt metabolit af l-[(2-bromphenyl)sulfonyl]-5-methoxy-3-[(4-methyl-l- piperazinyl)methyl] -1 H-indol-dimesylat-monohydrat er 1 - [(2-bromphenyl) sulfonyl] -5- methoxy-3-[(l-piperazinyl)methyl]-lH-indol med formlen (I),
2. Fremgangsmåde til fremstilling af en forbindelse med formlen (I) ifølge krav 1, der omfatter: Trin (i): omsætning af N-Boc-piperazin med formlen 1
i tilstedeværelse af eddikesyre og vandigt formaldehyd med formlen 2 for at opnå Mannich-addukt: HCHO 2 Trin (ii): omsætning af Mannich-adduktet med 5-methoxy-indol med formlen 3
i tilstedeværelse af methanol for at opnå 3-[(l-butyloxycarbonyl-piperazin-4-yl)methyl]-5-methoxy-lH-indol med formlen 4;
Trin (iii): oprensning af 3-[(l-t-butyloxycarbonylpiperazin-4-yl)methyl]-5-methoxy-lH-indol med formlen 4 ved anvendelse af n-hexan;
Trin (iv): omsætning af ovenfor opnåede 3-[(l-t-butyloxycarbonylpiperazin-4-yl)methyl]-5-methoxy-lH-indol med formlen 4 med 2-bromphenylsulfonylchlorid med formlen 5;
i tetrahydrofuran i tilstedeværelse af kaliumhydroxid for at opnå l-[(2-bromphenyl)sulfonyl]-5-methoxy-3-[(l-t-butyloxy-carbonyl-piperazin-4-yl)methyl]-lH-indol med formlen 6;
Trin (v): oprensning af l-[(2-bromphenyl)sulfonyl]-5-methoxy-3-[(l-t- butyloxycarbonylpiperazin-4-yl)methyl]-lH-indol med formlen 6 ved anvendelse af isopropanol og methanol; Trin (vi): omdannelse af ovenfor opnåede l-[(2-bromphenyl)sulfonyl]-5-methoxy-3-[(l-t-butyloxycarbonylpiperazin-4-yl)methyl]-lH-indol med formlen 6 i tilstedeværelse af absolut ethanol og vandig saltsyre for at opnå l-[(2-bromphenyl)sulfonyl]-5-methoxy-3-[(l-piperazinyl)methyl]-lH-indol-dihydrochlorid med formlen 8;
Trin (vii): ovenfor opnåede 1 - [(2-bromphenyl) sulfonyl] -5-methoxy-3 - [(piperazin-1 -yl)methyl]-lH-indoldihydrochlorid med formlen 8 opløses i vand og gøres basisk til pH 10,5 til 11 ved tilsætning af 40 % (vægt/vægt) lud for at opnå l-[(2-bromphenyl)sulfonyl]-5-methoxy-3-[(l-piperazinyl)methyl]-lH-indol med formlen (I).
3. Forbindelse med den almene formel (Π),
4. Fremgangsmåde til fremstilling af en forbindelse med formlen (II) ifølge krav 3, der omfatter: Trin (i): omsætning af N-Boc-piperazin med formlen 1
i tilstedeværelse af eddikesyre og vandigt formaldehyd med formlen 2 for at opnå Mannich-addukt; HCHO 2 Trin (ii): omsætning af Mannich-adduktet med 5-methoxyindol med formlen 3
i tilstedeværelse af methanol for at opnå 3-[(l-t-butyloxycarbonylpiperazin-4-yl)methyl]-5-methoxy-lH-indol med formlen 4;
Trin (iii): oprensning af 3-[(l-t-butyloxycarbonylpiperazin-4-yl)methyl]-5-methoxy-lH-indol med formlen 4 ved anvendelse af n-hexan; Trin (iv): omsætning af ovenfor opnåede 3-[(l-t-butyloxycarbonylpiperazin-4-yl)methyl]-5-methoxy-lH-indol med formlen 4 med 2-bromphenylsulfonylchlorid med formlen 5;
i tetrahydrofuran i tilstedeværelse af kaliumhydroxid for at opnå l-[(2-bromphenyl)sulfonyl]-5-methoxy-3-[(l-t-butyloxycarbonylpiperazin-4-yl)methyl]-lH-indol med formlen 6;
Trin (v): oprensning af l-[(2-bromphenyl)sulfonyl]-5-methoxy-3-[(l-t- butyloxycarbonylpiperazin-4-yl)methyl]-lH-indol med formlen 6 ved anvendelse af isopropanol og methanol; Trin (vi): omdannelse af ovenfor opnåede l-[(2-bromphenyl)sulfonyl]-5-methoxy-3-[(l-t-butyloxycarbonylpiperazin-4-yl)methyl]-lH-indol med formlen 6 i tilstedeværelse af acetone og methansulfonsyre med formlen 7
for at opnå l-[(2-bromphenyl)sulfonyl]-5-methoxy-3-[(l-piperazinyl)methyl]-lH-indoldimesylat med formlen 9;
Trin (vii): ovenfor opnåede 1 -[(2-bromphenyl) sulfonyl] -5-methoxy-3- [(1 -piperazinyl)methyl] -lH-indoldimesylat med formlen 9 opløses i vand og acetone ved opvarmning til 55-60 °C for at opnå 1 - [(2-bromphenyl) sulfonyl] -5-methoxy-3-[( 1 -piperazinyl)methyl] - 1H- indoldimesylatdihydrat med formlen (II).
5. Farmaceutisk sammensætning, der omfatter en forbindelse ifølge krav 1 og farmaceutisk acceptable excipienser.
6. Farmaceutisk sammensætning ifølge krav 5 til anvendelse i behandlingen af Alzheimers sygdom, ADHD, Parkinsons sygdom og skizofreni.
7. Forbindelse ifølge krav 1 til anvendelse i behandlingen af sygdomme relateret til 5-HT6-receptor.
8. Forbindelse ifølge krav 7 til anvendelse, hvor sygdommene relateret til 5-ΗΤό receptor er valgt fra Alzheimers sygdom, ADHD, Parkinsons sygdom og skizofreni.
9. Farmaceutisk sammensætning, der omfatter en forbindelse ifølge krav 3 og farmaceutisk acceptable excipienser.
10. Farmaceutisk sammensætning ifølge krav 9 til anvendelse i behandlingen af Alzheimers sygdom, ADHD, Parkinsons sygdom og skizofreni.
11. Forbindelse ifølge krav 3 til anvendelse i behandlingen af sygdomme relateret til 5-HT6-receptor.
12. Forbindelse ifølge krav 11 til anvendelse, hvor sygdommene relateret til 5-HT6-receptor er valgt fra Alzheimers sygdom, ADHD, Parkinsons sygdom og skizofreni.
13. Forbindelse med formlen (I) ifølge krav 1 til fremstilling af et lægemiddel til behandling af en forstyrrelse i centralnervesystemet relateret til eller påvirket af 5-ΗΤό-recep torerne.
14. Forbindelse med formlen (II) ifølge krav 3 til fremstilling af et lægemiddel til behandling af en forstyrrelse i centralnervesystemet relateret til eller påvirket af 5-ΗΤό-recep torerne.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN4011CH2014 | 2014-08-16 | ||
| PCT/IN2014/000667 WO2016027276A1 (en) | 2014-08-16 | 2014-10-20 | Active metabolite of 1-[(2-bromophenyl) sulfonyl]-5-methoxy-3- [(4-methyl-1-piperazinyl) methyl]-1h-indole dimesylate monohydrate and dimesylate dihydrate salt of active metabolite |
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| EA036347B1 (ru) * | 2016-05-18 | 2020-10-29 | Сувен Лайф Сайенсиз Лимитед | Комбинация чистых антагонистов 5-ht6 рецепторов с ингибиторами ацетилхолинэстеразы |
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| JP4559230B2 (ja) * | 2002-11-28 | 2010-10-06 | スベン ライフ サイエンシズ リミティド | セロトニン受容体に対する親和性を有する新規ｎ−アリールスルホニル−３−置換されたインドール、その調製方法、それを含有する医薬組成物 |
| EA009367B1 (ru) * | 2002-12-18 | 2007-12-28 | Сувен Лайф Сайенсиз Лимитед | ПРОИЗВОДНЫЕ 5-ТИА-5-ДИОКСО-4b-АЗАИНДЕНО[2,1-a]ИНДЕНА, ОБЛАДАЮЩИЕ АФФИННОСТЬЮ К РЕЦЕПТОРУ СЕРОТОНИНА |
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