RU2471781C2 - Новые двузамещенные фенилпирролидины в качестве модуляторов кортикальной катехоламинергической нейротрансмиссии - Google Patents
Новые двузамещенные фенилпирролидины в качестве модуляторов кортикальной катехоламинергической нейротрансмиссии Download PDFInfo
- Publication number
- RU2471781C2 RU2471781C2 RU2009143104/04A RU2009143104A RU2471781C2 RU 2471781 C2 RU2471781 C2 RU 2471781C2 RU 2009143104/04 A RU2009143104/04 A RU 2009143104/04A RU 2009143104 A RU2009143104 A RU 2009143104A RU 2471781 C2 RU2471781 C2 RU 2471781C2
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- RU
- Russia
- Prior art keywords
- difluorophenyl
- ethylpyrrolidin
- pyrrolidin
- fluorophenyl
- chloro
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- VDQQJMHXZCMNMU-UHFFFAOYSA-N 1-phenylpyrrolidine Chemical class C1CCCN1C1=CC=CC=C1 VDQQJMHXZCMNMU-UHFFFAOYSA-N 0.000 title abstract 2
- 230000000768 catecholaminergic effect Effects 0.000 title 1
- 230000001054 cortical effect Effects 0.000 title 1
- 230000005062 synaptic transmission Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 15
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims abstract 14
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims abstract 14
- 150000003839 salts Chemical class 0.000 claims abstract 8
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 claims abstract 7
- 150000001204 N-oxides Chemical class 0.000 claims abstract 7
- 229960003638 dopamine Drugs 0.000 claims abstract 7
- 239000000203 mixture Substances 0.000 claims abstract 7
- 229960002748 norepinephrine Drugs 0.000 claims abstract 7
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 claims abstract 7
- 229940076279 serotonin Drugs 0.000 claims abstract 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract 2
- 208000015114 central nervous system disease Diseases 0.000 claims abstract 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims abstract 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- LJSQUPHAOKTMIR-UHFFFAOYSA-N 3-(2,3-difluorophenyl)-1-ethylpyrrolidin-3-ol Chemical compound C1N(CC)CCC1(O)C1=CC=CC(F)=C1F LJSQUPHAOKTMIR-UHFFFAOYSA-N 0.000 claims 3
- NCIWSEVOPAYAFW-UHFFFAOYSA-N 3-(3,4-difluorophenyl)-1-ethylpyrrolidin-3-ol Chemical compound C1N(CC)CCC1(O)C1=CC=C(F)C(F)=C1 NCIWSEVOPAYAFW-UHFFFAOYSA-N 0.000 claims 3
- LFOPWHXMDFGBCZ-UHFFFAOYSA-N 3-(3,4-difluorophenyl)-1-propylpyrrolidin-3-ol Chemical compound C1N(CCC)CCC1(O)C1=CC=C(F)C(F)=C1 LFOPWHXMDFGBCZ-UHFFFAOYSA-N 0.000 claims 3
- PZCIZLSHEPXHAY-UHFFFAOYSA-N 3-(3,5-difluorophenyl)-1-ethylpyrrolidin-3-ol Chemical compound C1N(CC)CCC1(O)C1=CC(F)=CC(F)=C1 PZCIZLSHEPXHAY-UHFFFAOYSA-N 0.000 claims 3
- SJBRVYCKTOKPMU-UHFFFAOYSA-N 3-(3,5-difluorophenyl)-1-methylpyrrolidin-3-ol Chemical compound C1N(C)CCC1(O)C1=CC(F)=CC(F)=C1 SJBRVYCKTOKPMU-UHFFFAOYSA-N 0.000 claims 3
- ZCCVFEZXNYDPFH-UHFFFAOYSA-N 3-(3,5-difluorophenyl)-1-propylpyrrolidin-3-ol Chemical compound C1N(CCC)CCC1(O)C1=CC(F)=CC(F)=C1 ZCCVFEZXNYDPFH-UHFFFAOYSA-N 0.000 claims 3
- VUYBUSQWWQWBAX-UHFFFAOYSA-N 3-(3-chloro-2-fluorophenyl)-1-ethylpyrrolidin-3-ol Chemical compound C1N(CC)CCC1(O)C1=CC=CC(Cl)=C1F VUYBUSQWWQWBAX-UHFFFAOYSA-N 0.000 claims 3
- ZNMYFXMWLGTUBE-UHFFFAOYSA-N 3-(3-chloro-2-fluorophenyl)-1-methylpyrrolidin-3-ol Chemical compound C1N(C)CCC1(O)C1=CC=CC(Cl)=C1F ZNMYFXMWLGTUBE-UHFFFAOYSA-N 0.000 claims 3
- NIGZAKLAUVDBKT-UHFFFAOYSA-N 3-(3-chloro-5-fluorophenyl)-1-ethylpyrrolidin-3-ol Chemical compound C1N(CC)CCC1(O)C1=CC(F)=CC(Cl)=C1 NIGZAKLAUVDBKT-UHFFFAOYSA-N 0.000 claims 3
- XYFCSWGDPHKZKM-UHFFFAOYSA-N 3-(3-chloro-5-fluorophenyl)-1-methylpyrrolidin-3-ol Chemical compound C1N(C)CCC1(O)C1=CC(F)=CC(Cl)=C1 XYFCSWGDPHKZKM-UHFFFAOYSA-N 0.000 claims 3
- 210000003169 central nervous system Anatomy 0.000 claims 3
- 208000010877 cognitive disease Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- QDFWOUONMZLLJG-UHFFFAOYSA-N 1-(cyclopropylmethyl)-3-(2,3-difluorophenyl)pyrrolidin-3-ol Chemical compound C1C(O)(C=2C(=C(F)C=CC=2)F)CCN1CC1CC1 QDFWOUONMZLLJG-UHFFFAOYSA-N 0.000 claims 2
- UEBPNMSACCRKBW-UHFFFAOYSA-N 1-butyl-3-(2,3-difluorophenyl)pyrrolidin-3-ol Chemical compound C1N(CCCC)CCC1(O)C1=CC=CC(F)=C1F UEBPNMSACCRKBW-UHFFFAOYSA-N 0.000 claims 2
- KYLAQLWJVQYHFE-UHFFFAOYSA-N 1-butyl-3-(3,5-difluorophenyl)pyrrolidin-3-ol Chemical compound C1N(CCCC)CCC1(O)C1=CC(F)=CC(F)=C1 KYLAQLWJVQYHFE-UHFFFAOYSA-N 0.000 claims 2
- NHQBQIQRZDBVFY-UHFFFAOYSA-N 3-(2,3-difluorophenyl)-1-(2-methylpropyl)pyrrolidin-3-ol Chemical compound C1N(CC(C)C)CCC1(O)C1=CC=CC(F)=C1F NHQBQIQRZDBVFY-UHFFFAOYSA-N 0.000 claims 2
- JSQSGEOUGAKKCB-UHFFFAOYSA-N 3-(2,3-difluorophenyl)-1-(3,3,3-trifluoropropyl)pyrrolidin-3-ol Chemical compound C=1C=CC(F)=C(F)C=1C1(O)CCN(CCC(F)(F)F)C1 JSQSGEOUGAKKCB-UHFFFAOYSA-N 0.000 claims 2
- XYBMKKZXZVSIEC-UHFFFAOYSA-N 3-(2,3-difluorophenyl)-1-methylpyrrolidin-3-ol Chemical compound C1N(C)CCC1(O)C1=CC=CC(F)=C1F XYBMKKZXZVSIEC-UHFFFAOYSA-N 0.000 claims 2
- QQMUFVZGYVONBS-UHFFFAOYSA-N 3-(2,3-difluorophenyl)-1-prop-2-enylpyrrolidin-3-ol Chemical compound C=1C=CC(F)=C(F)C=1C1(O)CCN(CC=C)C1 QQMUFVZGYVONBS-UHFFFAOYSA-N 0.000 claims 2
- NCYIYMVGKMWQLA-UHFFFAOYSA-N 3-(2,3-difluorophenyl)-1-propylpyrrolidin-3-ol Chemical compound C1N(CCC)CCC1(O)C1=CC=CC(F)=C1F NCYIYMVGKMWQLA-UHFFFAOYSA-N 0.000 claims 2
- CCJZNYJTLCONPI-UHFFFAOYSA-N 3-(3,5-difluorophenyl)-1-(2-methoxyethyl)pyrrolidin-3-ol Chemical compound C1N(CCOC)CCC1(O)C1=CC(F)=CC(F)=C1 CCJZNYJTLCONPI-UHFFFAOYSA-N 0.000 claims 2
- SYUUBVPTDUWJOY-UHFFFAOYSA-N 3-(3,5-difluorophenyl)-1-(2-methylpropyl)pyrrolidin-3-ol Chemical compound C1N(CC(C)C)CCC1(O)C1=CC(F)=CC(F)=C1 SYUUBVPTDUWJOY-UHFFFAOYSA-N 0.000 claims 2
- PYDSFTRKWFHUTI-UHFFFAOYSA-N 3-(3,5-difluorophenyl)-1-prop-2-enylpyrrolidin-3-ol Chemical compound C=1C(F)=CC(F)=CC=1C1(O)CCN(CC=C)C1 PYDSFTRKWFHUTI-UHFFFAOYSA-N 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- -1 2,3-difluorophenyl Chemical group 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- USWSHXCFJJSHDE-UHFFFAOYSA-N 3-(2,3-dichlorophenyl)-1-ethylpyrrolidin-3-ol Chemical compound C1N(CC)CCC1(O)C1=CC=CC(Cl)=C1Cl USWSHXCFJJSHDE-UHFFFAOYSA-N 0.000 claims 1
- WGXFCVDUBAPUSV-UHFFFAOYSA-N 3-(2,3-difluorophenyl)-1-(2-methoxyethyl)pyrrolidin-3-ol Chemical compound C1N(CCOC)CCC1(O)C1=CC=CC(F)=C1F WGXFCVDUBAPUSV-UHFFFAOYSA-N 0.000 claims 1
- CQRPFHDPCOFOIL-UHFFFAOYSA-N 3-(2,3-difluorophenyl)-3-fluoropyrrolidine Chemical compound FC1=CC=CC(C2(F)CNCC2)=C1F CQRPFHDPCOFOIL-UHFFFAOYSA-N 0.000 claims 1
- NVJZWXSTCVALIX-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-1-methylpyrrolidin-3-ol Chemical compound C1N(C)CCC1(O)C1=CC=C(F)C=C1F NVJZWXSTCVALIX-UHFFFAOYSA-N 0.000 claims 1
- AYFLLPMVZQVMIM-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-1-ethylpyrrolidin-3-ol Chemical compound C1N(CC)CCC1(O)C1=CC=C(Cl)C(Cl)=C1 AYFLLPMVZQVMIM-UHFFFAOYSA-N 0.000 claims 1
- RZPNURHRNBRHQL-UHFFFAOYSA-N 3-(3,4-difluorophenyl)-1-methylpyrrolidin-3-ol Chemical compound C1N(C)CCC1(O)C1=CC=C(F)C(F)=C1 RZPNURHRNBRHQL-UHFFFAOYSA-N 0.000 claims 1
- RAFSLGNAHYYRST-UHFFFAOYSA-N 3-(3,4-difluorophenyl)-1-propan-2-ylpyrrolidin-3-ol Chemical compound C1N(C(C)C)CCC1(O)C1=CC=C(F)C(F)=C1 RAFSLGNAHYYRST-UHFFFAOYSA-N 0.000 claims 1
- ZJOAAWUEZFVQHP-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-1-ethylpyrrolidin-3-ol Chemical compound C1N(CC)CCC1(O)C1=CC(Cl)=CC(Cl)=C1 ZJOAAWUEZFVQHP-UHFFFAOYSA-N 0.000 claims 1
- MTSVWPYXOZDKAU-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-3-fluoropyrrolidine Chemical compound C=1C(Cl)=CC(Cl)=CC=1C1(F)CCNC1 MTSVWPYXOZDKAU-UHFFFAOYSA-N 0.000 claims 1
- VAYCSAOIQFQZJH-UHFFFAOYSA-N 3-(3,5-difluorophenyl)-3-fluoro-1-methylpyrrolidine Chemical compound C1N(C)CCC1(F)C1=CC(F)=CC(F)=C1 VAYCSAOIQFQZJH-UHFFFAOYSA-N 0.000 claims 1
- PDOGFKRZZSBEGE-UHFFFAOYSA-N 3-(3,5-difluorophenyl)-3-fluoropyrrolidine Chemical compound FC1=CC(F)=CC(C2(F)CNCC2)=C1 PDOGFKRZZSBEGE-UHFFFAOYSA-N 0.000 claims 1
- SSWRIHFVYMUNQR-UHFFFAOYSA-N 3-(3-chloro-4-fluorophenyl)-1-ethylpyrrolidin-3-ol Chemical compound C1N(CC)CCC1(O)C1=CC=C(F)C(Cl)=C1 SSWRIHFVYMUNQR-UHFFFAOYSA-N 0.000 claims 1
- UALDFWPLQVYDFB-UHFFFAOYSA-N 3-(3-chloro-4-fluorophenyl)-1-propylpyrrolidin-3-ol Chemical compound C1N(CCC)CCC1(O)C1=CC=C(F)C(Cl)=C1 UALDFWPLQVYDFB-UHFFFAOYSA-N 0.000 claims 1
- DRHLAPLUKBFHAQ-UHFFFAOYSA-N 3-(3-chloro-5-fluorophenyl)-1-propylpyrrolidin-3-ol Chemical compound C1N(CCC)CCC1(O)C1=CC(F)=CC(Cl)=C1 DRHLAPLUKBFHAQ-UHFFFAOYSA-N 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
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- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000029560 autism spectrum disease Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
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- 229940079593 drug Drugs 0.000 claims 1
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- 238000000034 method Methods 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D207/12—Oxygen or sulfur atoms
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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
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- 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
- 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
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- 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
- A61P25/20—Hypnotics; Sedatives
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- 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
- A61P25/22—Anxiolytics
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- 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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- 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
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- A—HUMAN NECESSITIES
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- 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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- Bioinformatics & Cheminformatics (AREA)
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- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
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- Hospice & Palliative Care (AREA)
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- Anesthesiology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0701387 | 2007-06-05 | ||
| SE0701387-3 | 2007-06-05 | ||
| PCT/EP2008/056915 WO2008148801A2 (en) | 2007-06-05 | 2008-06-04 | Disubstituted phenylpyrrolidines as modulators of cortical catecholaminergic neurotransmission |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2009143104A RU2009143104A (ru) | 2011-07-20 |
| RU2471781C2 true RU2471781C2 (ru) | 2013-01-10 |
Family
ID=39743744
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2009143104/04A RU2471781C2 (ru) | 2007-06-05 | 2008-06-04 | Новые двузамещенные фенилпирролидины в качестве модуляторов кортикальной катехоламинергической нейротрансмиссии |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8188301B2 (enExample) |
| EP (1) | EP2155671B8 (enExample) |
| JP (1) | JP5444535B2 (enExample) |
| KR (1) | KR20100038295A (enExample) |
| CN (1) | CN101808987A (enExample) |
| AU (1) | AU2008258599B2 (enExample) |
| BR (1) | BRPI0812740A2 (enExample) |
| CA (1) | CA2690091A1 (enExample) |
| CO (1) | CO6251288A2 (enExample) |
| IL (1) | IL202045A0 (enExample) |
| MX (1) | MX2009012787A (enExample) |
| NZ (1) | NZ581364A (enExample) |
| RU (1) | RU2471781C2 (enExample) |
| UA (1) | UA98783C2 (enExample) |
| WO (1) | WO2008148801A2 (enExample) |
| ZA (1) | ZA200908592B (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8188301B2 (en) | 2007-06-05 | 2012-05-29 | Nsab, Filial Af Neurosearch Sweden Ab, Sverige | Disubstituted phenylpyrrolidines as modulators of cortical catecholaminergic neurotransmission |
| JP5716202B2 (ja) | 2008-11-24 | 2015-05-13 | インテグレイティブ・リサーチ・ラボラトリーズ・スウェーデン・アーベー | 皮質のカテコールアミン作動性神経伝達のモジュレーターとしての３−フェニル−３−メトキシピロリジン誘導体 |
| EP2367785B1 (en) | 2008-11-24 | 2014-10-15 | Integrative Research Laboratories Sweden AB | Novel 3-phenyl-azetidine derivatives useful as modulators of cortical catecholaminergic neurotransmission |
| WO2010058020A1 (en) * | 2008-11-24 | 2010-05-27 | Nsab, Filial Af Neurosearch Sweden Ab, Sverige | Novel 1 -alkyl- 3 -hydroxy- 3 -phenylazetidine derivatives useful as modulators of cortical catecholaminergic neurotransmission |
| SG171914A1 (en) | 2008-12-02 | 2011-07-28 | Chiralgen Ltd | Method for the synthesis of phosphorus atom modified nucleic acids |
| TW201026666A (en) * | 2008-12-16 | 2010-07-16 | Astrazeneca Ab | Quaternary piperidine derivatives and uses thereof |
| EP2451461A4 (en) | 2009-07-06 | 2013-05-29 | Ontorii Inc | NOVEL NUCLEIC ACID PRODRUGS AND METHOD OF USE THEREOF |
| DK2620428T3 (da) * | 2010-09-24 | 2019-07-01 | Wave Life Sciences Ltd | Asymmetrisk hjælpegruppe |
| US9605019B2 (en) | 2011-07-19 | 2017-03-28 | Wave Life Sciences Ltd. | Methods for the synthesis of functionalized nucleic acids |
| CN112007045B (zh) | 2012-07-13 | 2026-01-06 | 波涛生命科学有限公司 | 手性控制 |
| DK2872485T3 (da) | 2012-07-13 | 2021-03-08 | Wave Life Sciences Ltd | Asymmetrisk hjælpegruppe |
| JP6246121B2 (ja) | 2012-07-13 | 2017-12-13 | 株式会社新日本科学 | キラル核酸アジュバント |
| WO2015108048A1 (ja) | 2014-01-15 | 2015-07-23 | 株式会社新日本科学 | 抗腫瘍作用を有するキラル核酸アジュバンド及び抗腫瘍剤 |
| US10322173B2 (en) | 2014-01-15 | 2019-06-18 | Shin Nippon Biomedical Laboratories, Ltd. | Chiral nucleic acid adjuvant having anti-allergic activity, and anti-allergic agent |
| EP3095461A4 (en) | 2014-01-15 | 2017-08-23 | Shin Nippon Biomedical Laboratories, Ltd. | Chiral nucleic acid adjuvant having immunity induction activity, and immunity induction activator |
| KR102423317B1 (ko) | 2014-01-16 | 2022-07-22 | 웨이브 라이프 사이언시스 리미티드 | 키랄 디자인 |
| EP3297987B1 (en) * | 2015-05-20 | 2019-05-15 | Integrative Research Laboratories Sweden AB | Novel azetidine derivatives useful as modulators of cortical cathecolaminergic neurotransmission |
| ES2805031T3 (es) | 2016-02-10 | 2021-02-10 | Sumitomo Chemical Co | Método de producción de 1-metilpirrolidin-3-ol |
| JP7126522B2 (ja) | 2017-05-19 | 2022-08-26 | インテグレイティブ・リサーチ・ラボラトリーズ・スウェーデン・アーベー | （＋）－３－（２，３－ジフルオロフェニル）－３－メトキシピロリジンまたはその薬学的に許容される塩、それを調製するための方法およびその使用 |
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- 2008-06-04 AU AU2008258599A patent/AU2008258599B2/en not_active Expired - Fee Related
- 2008-06-04 UA UAA200911475A patent/UA98783C2/ru unknown
- 2008-06-04 JP JP2010510783A patent/JP5444535B2/ja not_active Expired - Fee Related
- 2008-06-04 EP EP08760496.3A patent/EP2155671B8/en not_active Not-in-force
- 2008-06-04 CA CA2690091A patent/CA2690091A1/en not_active Abandoned
- 2008-06-04 BR BRPI0812740A patent/BRPI0812740A2/pt not_active IP Right Cessation
- 2008-06-04 MX MX2009012787A patent/MX2009012787A/es active IP Right Grant
- 2008-06-04 WO PCT/EP2008/056915 patent/WO2008148801A2/en not_active Ceased
- 2008-06-04 RU RU2009143104/04A patent/RU2471781C2/ru not_active IP Right Cessation
- 2008-06-04 CN CN200880018820A patent/CN101808987A/zh active Pending
- 2008-06-04 NZ NZ581364A patent/NZ581364A/en not_active IP Right Cessation
- 2008-06-04 KR KR1020097025393A patent/KR20100038295A/ko not_active Withdrawn
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Also Published As
| Publication number | Publication date |
|---|---|
| US20100179211A1 (en) | 2010-07-15 |
| WO2008148801A8 (en) | 2009-12-10 |
| AU2008258599B2 (en) | 2013-06-13 |
| RU2009143104A (ru) | 2011-07-20 |
| EP2155671A2 (en) | 2010-02-24 |
| KR20100038295A (ko) | 2010-04-14 |
| CA2690091A1 (en) | 2008-12-11 |
| UA98783C2 (en) | 2012-06-25 |
| EP2155671B1 (en) | 2017-12-20 |
| AU2008258599A1 (en) | 2008-12-11 |
| US8188301B2 (en) | 2012-05-29 |
| NZ581364A (en) | 2011-10-28 |
| IL202045A0 (en) | 2010-06-16 |
| CO6251288A2 (es) | 2011-02-21 |
| WO2008148801A3 (en) | 2009-01-29 |
| MX2009012787A (es) | 2009-12-15 |
| CN101808987A (zh) | 2010-08-18 |
| JP2010529081A (ja) | 2010-08-26 |
| JP5444535B2 (ja) | 2014-03-19 |
| WO2008148801A2 (en) | 2008-12-11 |
| ZA200908592B (en) | 2011-02-23 |
| EP2155671B8 (en) | 2018-02-21 |
| BRPI0812740A2 (pt) | 2016-07-19 |
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