JP2010529081A5 - - Google Patents
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- Publication number
- JP2010529081A5 JP2010529081A5 JP2010510783A JP2010510783A JP2010529081A5 JP 2010529081 A5 JP2010529081 A5 JP 2010529081A5 JP 2010510783 A JP2010510783 A JP 2010510783A JP 2010510783 A JP2010510783 A JP 2010510783A JP 2010529081 A5 JP2010529081 A5 JP 2010529081A5
- Authority
- JP
- Japan
- Prior art keywords
- difluorophenyl
- ethylpyrrolidin
- pyrrolidin
- fluorophenyl
- chloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 7
- 150000001204 N-oxides Chemical class 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 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
- 208000010877 cognitive disease Diseases 0.000 claims 3
- 201000000980 schizophrenia Diseases 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
- 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 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
- 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
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- 208000011688 Generalised anxiety disease Diseases 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 208000015114 central nervous system disease Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 208000029364 generalized anxiety disease Diseases 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 208000019906 panic disease Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 claims 1
- -1 2,3-difluorophenyl Chemical group 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([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
- 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 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
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 208000012239 Developmental disease Diseases 0.000 claims 1
- 208000027534 Emotional disease Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 206010034912 Phobia Diseases 0.000 claims 1
- 208000029560 autism spectrum disease Diseases 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 206010008129 cerebral palsy Diseases 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000010249 dopaminergic function Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 208000019116 sleep disease Diseases 0.000 claims 1
- 208000020685 sleep-wake disease Diseases 0.000 claims 1
- 201000001716 specific phobia Diseases 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 208000011580 syndromic disease Diseases 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
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 0 *C1(CN(*)CC1)c1cc(*)cc(*)c1 Chemical compound *C1(CN(*)CC1)c1cc(*)cc(*)c1 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94199407P | 2007-06-05 | 2007-06-05 | |
| SE0701387-3 | 2007-06-05 | ||
| US60/941,994 | 2007-06-05 | ||
| SE0701387 | 2007-06-05 | ||
| PCT/EP2008/056915 WO2008148801A2 (en) | 2007-06-05 | 2008-06-04 | Disubstituted phenylpyrrolidines as modulators of cortical catecholaminergic neurotransmission |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010529081A JP2010529081A (ja) | 2010-08-26 |
| JP2010529081A5 true JP2010529081A5 (OSRAM) | 2011-07-14 |
| JP5444535B2 JP5444535B2 (ja) | 2014-03-19 |
Family
ID=39743744
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010510783A Expired - Fee Related JP5444535B2 (ja) | 2007-06-05 | 2008-06-04 | 皮質カテコールアミン作動性神経伝達の調節物質としての新規な二置換フェニルピロリジン |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8188301B2 (OSRAM) |
| EP (1) | EP2155671B8 (OSRAM) |
| JP (1) | JP5444535B2 (OSRAM) |
| KR (1) | KR20100038295A (OSRAM) |
| CN (1) | CN101808987A (OSRAM) |
| AU (1) | AU2008258599B2 (OSRAM) |
| BR (1) | BRPI0812740A2 (OSRAM) |
| CA (1) | CA2690091A1 (OSRAM) |
| CO (1) | CO6251288A2 (OSRAM) |
| IL (1) | IL202045A0 (OSRAM) |
| MX (1) | MX2009012787A (OSRAM) |
| NZ (1) | NZ581364A (OSRAM) |
| RU (1) | RU2471781C2 (OSRAM) |
| UA (1) | UA98783C2 (OSRAM) |
| WO (1) | WO2008148801A2 (OSRAM) |
| ZA (1) | ZA200908592B (OSRAM) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2155671B8 (en) | 2007-06-05 | 2018-02-21 | Integrative Research Laboratories Sweden AB | Disubstituted phenylpyrrolidines as modulators of cortical catecholaminergic neurotransmission |
| NZ592566A (en) | 2008-11-24 | 2013-03-28 | Nsab Af Neurosearch Sweden Ab | 3-phenyl-3-methoxypyrrolidine derivatives as modulators of cortical catecholaminergic neurotransmission |
| 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 |
| US20110257148A1 (en) * | 2008-11-24 | 2011-10-20 | Nsab, Filial Af Neurosearch Sweden Ab, Sverige | Novel 1-alkyl-3-hydroxy-3-phenylazetidine derivatives useful as modulators of cortical catecholaminergic neurotransmission |
| KR101881596B1 (ko) | 2008-12-02 | 2018-07-24 | 웨이브 라이프 사이언시스 재팬 인코포레이티드 | 인 원자 변형된 핵산의 합성 방법 |
| WO2010071575A1 (en) * | 2008-12-16 | 2010-06-24 | Astrazeneca Ab | Quaternary piperidine derivatives and uses thereof |
| RU2612521C2 (ru) | 2009-07-06 | 2017-03-09 | Онтории, Инк. | Новые пролекарства нуклеиновых кислот и способы их применения |
| JP5868324B2 (ja) * | 2010-09-24 | 2016-02-24 | 株式会社Wave Life Sciences Japan | 不斉補助基 |
| BR112014001244A2 (pt) | 2011-07-19 | 2017-02-21 | Wave Life Sciences Pte Ltd | métodos para a síntese de ácidos nucléicos funcionalizados |
| ES2862073T3 (es) | 2012-07-13 | 2021-10-06 | Wave Life Sciences Ltd | Grupo auxiliar asimétrico |
| BR112015000723A2 (pt) | 2012-07-13 | 2017-06-27 | Shin Nippon Biomedical Laboratories Ltd | adjuvante de ácido nucléico quiral |
| CN112007045A (zh) | 2012-07-13 | 2020-12-01 | 波涛生命科学有限公司 | 手性控制 |
| EP3095459A4 (en) | 2014-01-15 | 2017-08-23 | Shin Nippon Biomedical Laboratories, Ltd. | Chiral nucleic acid adjuvant having antitumor effect and antitumor agent |
| EP3095460A4 (en) | 2014-01-15 | 2017-08-23 | Shin Nippon Biomedical Laboratories, Ltd. | Chiral nucleic acid adjuvant having anti-allergic activity, and anti-allergic agent |
| US10144933B2 (en) | 2014-01-15 | 2018-12-04 | Shin Nippon Biomedical Laboratories, Ltd. | Chiral nucleic acid adjuvant having immunity induction activity, and immunity induction activator |
| CN113278617A (zh) | 2014-01-16 | 2021-08-20 | 波涛生命科学有限公司 | 手性设计 |
| NZ737451A (en) | 2015-05-20 | 2022-01-28 | Integrative Res Laboratories Sweden Ab | Novel azetidine derivatives useful as modulators of cortical catecholaminergic neurotransmission |
| ES2805031T3 (es) | 2016-02-10 | 2021-02-10 | Sumitomo Chemical Co | Método de producción de 1-metilpirrolidin-3-ol |
| ES2943252T3 (es) | 2017-05-19 | 2023-06-12 | Integrative Res Laboratories Sweden Ab | Fumarato de (+)-3-(2,3-difluorofenil)-3-metoxipirrolidina, un proceso para su preparación y sus usos |
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| US2878264A (en) * | 1959-03-17 | Substituted amino alcohols | ||
| CH372667A (de) | 1957-09-26 | 1963-10-31 | Robins Co Inc A H | Verfahren zur Herstellung von 3-Aryl-3-pyrrolidinolen |
| US3118907A (en) * | 1961-08-14 | 1964-01-21 | Mead Johnson & Co | 3-substituted-3-pyrrolidinols |
| BE704683A (OSRAM) | 1966-11-07 | 1968-02-15 | ||
| US3635982A (en) * | 1969-04-08 | 1972-01-18 | American Home Prod | Amino-substituted-quinoxalinyloxazolidines and -oxazines |
| US5128362A (en) * | 1988-01-15 | 1992-07-07 | Abbott Laboratories | 1-aminomethyl-1,2,3,4-tetrahydronaphthalenes |
| DE3802175A1 (de) | 1988-01-26 | 1989-08-03 | Hoechst Ag | N-phenylbenzamide und n-phenylbenzamidoxime, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung als schaedlingsbekaempfungsmittel |
| DE3835291A1 (de) * | 1988-04-19 | 1989-11-02 | Bayer Ag | 1,3-disubstituierte pyrrolidine |
| US5444083A (en) * | 1989-02-03 | 1995-08-22 | Eisai Co., Ltd. | Pyrrolidine compound and pharmaceutical use |
| CA2105666C (en) * | 1991-04-17 | 2006-02-14 | Kjell Anders Ivan Svensson | New centrally acting substituted phenylazacycloalkanes |
| EP0586229A1 (en) * | 1992-09-01 | 1994-03-09 | Zeneca Limited | 3-Hydroxy-3-(subst-akyl)-pyrrolidines as 5-lipoxygenase inhibitors |
| US5665754A (en) * | 1993-09-20 | 1997-09-09 | Glaxo Wellcome Inc. | Substituted pyrrolidines |
| WO1997024325A1 (en) | 1995-12-28 | 1997-07-10 | Takeda Chemical Industries, Ltd. | DIPHENYLMETHANE DERIVATIVES AS MIP-1α/RANTES RECEPTOR ANTAGONISTS |
| CA2338209A1 (en) | 1998-07-20 | 2000-02-03 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Biphenyl derivatives |
| US20020169155A1 (en) * | 1998-09-04 | 2002-11-14 | Millennium Pharmaceuticals, Inc. | Chemokine receptor anagonists and methods of use therefor |
| US7271176B2 (en) * | 1998-09-04 | 2007-09-18 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use thereof |
| DE19840611A1 (de) * | 1998-09-05 | 2000-03-09 | Klaus Wanner | GABA-uptake-Inhibitoren mit Pyrrolidinstruktur |
| WO2000070417A1 (en) | 1999-05-17 | 2000-11-23 | The Foxboro Company | Process control configuration system with parameterized objects |
| ECSP003637A (es) | 1999-08-31 | 2002-03-25 | Agouron Pharma | Inhibidores triciclicos de poli (adp-ribosa) polimerasas |
| SE9904723D0 (sv) | 1999-12-22 | 1999-12-22 | Carlsson A Research Ab | New modulators of dopamine neurotransmission II |
| JP4765627B2 (ja) * | 2003-09-22 | 2011-09-07 | Ｍｓｄ株式会社 | 新規ピペリジン誘導体 |
| SE0401465D0 (sv) * | 2004-06-08 | 2004-06-08 | Carlsson A Research Ab | New substituted piperdines as modulators of dopamine neurotransmission |
| US7700587B2 (en) * | 2004-09-07 | 2010-04-20 | Florida A&M University | Haloperidol analogs |
| US7598279B2 (en) | 2005-04-22 | 2009-10-06 | Sk Holdings Co., Ltd. | Neurotherapeutic azole compounds |
| JP2008540395A (ja) | 2005-05-03 | 2008-11-20 | ファイザー・インク | アミドレソルシノール化合物 |
| WO2007053145A1 (en) | 2005-11-04 | 2007-05-10 | Florida A & M University | Haloperidol analogs |
| EP1966164B1 (en) | 2005-12-21 | 2013-03-06 | Janssen Pharmaceutica N.V. | Novel substituted pyrazinone derivatives for use in mch-1 mediated diseases |
| EP2155671B8 (en) | 2007-06-05 | 2018-02-21 | Integrative Research Laboratories Sweden AB | Disubstituted phenylpyrrolidines as modulators of cortical catecholaminergic neurotransmission |
| CA2689692A1 (en) | 2007-06-05 | 2008-12-11 | Clas Sonesson | New disubstituted phenylpyrrolidines as modulators of cortical catecholaminergic neurotransmission |
-
2008
- 2008-06-04 EP EP08760496.3A patent/EP2155671B8/en not_active Not-in-force
- 2008-06-04 UA UAA200911475A patent/UA98783C2/ru unknown
- 2008-06-04 US US12/663,223 patent/US8188301B2/en not_active Expired - Fee Related
- 2008-06-04 RU RU2009143104/04A patent/RU2471781C2/ru not_active IP Right Cessation
- 2008-06-04 BR BRPI0812740A patent/BRPI0812740A2/pt not_active IP Right Cessation
- 2008-06-04 JP JP2010510783A patent/JP5444535B2/ja not_active Expired - Fee Related
- 2008-06-04 KR KR1020097025393A patent/KR20100038295A/ko not_active Withdrawn
- 2008-06-04 AU AU2008258599A patent/AU2008258599B2/en not_active Expired - Fee Related
- 2008-06-04 NZ NZ581364A patent/NZ581364A/en not_active IP Right Cessation
- 2008-06-04 CN CN200880018820A patent/CN101808987A/zh active Pending
- 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 CA CA2690091A patent/CA2690091A1/en not_active Abandoned
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2009
- 2009-11-11 IL IL202045A patent/IL202045A0/en unknown
- 2009-12-03 ZA ZA2009/08592A patent/ZA200908592B/en unknown
- 2009-12-18 CO CO09145364A patent/CO6251288A2/es not_active Application Discontinuation
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