JP2007502783A5 - - Google Patents
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- Publication number
- JP2007502783A5 JP2007502783A5 JP2006523528A JP2006523528A JP2007502783A5 JP 2007502783 A5 JP2007502783 A5 JP 2007502783A5 JP 2006523528 A JP2006523528 A JP 2006523528A JP 2006523528 A JP2006523528 A JP 2006523528A JP 2007502783 A5 JP2007502783 A5 JP 2007502783A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- salt
- free base
- malonate
- 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 description 54
- 239000000843 powder Substances 0.000 claims description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 36
- 150000003839 salts Chemical class 0.000 claims 31
- 239000012458 free base Substances 0.000 claims 10
- 238000004519 manufacturing process Methods 0.000 claims 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- PIPWSBOFSUJCCO-UHFFFAOYSA-N 2,2-dimethylpiperazine Chemical compound CC1(C)CNCCN1 PIPWSBOFSUJCCO-UHFFFAOYSA-N 0.000 claims 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 5
- 208000028017 Psychotic disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 201000000980 schizophrenia Diseases 0.000 claims 5
- 239000002904 solvent Substances 0.000 claims 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 3
- 239000002585 base Substances 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 3
- 229920000856 Amylose Polymers 0.000 claims 2
- 208000027534 Emotional disease Diseases 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical compound NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 150000001335 aliphatic alkanes Chemical group 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- OFOBLEOULBTSOW-UHFFFAOYSA-M malonate(1-) Chemical compound OC(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-M 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 238000006268 reductive amination reaction Methods 0.000 claims 2
- 150000003335 secondary amines Chemical class 0.000 claims 2
- 239000000741 silica gel Substances 0.000 claims 2
- 229910002027 silica gel Inorganic materials 0.000 claims 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- SBTVLCPCSXMWIQ-UHFFFAOYSA-N (3,5-dimethylphenyl) carbamate Chemical compound CC1=CC(C)=CC(OC(N)=O)=C1 SBTVLCPCSXMWIQ-UHFFFAOYSA-N 0.000 claims 1
- RFAPOGMFZTYBEW-UHFFFAOYSA-N 1,2,2-trimethylpiperazine Chemical compound CN1CCNCC1(C)C RFAPOGMFZTYBEW-UHFFFAOYSA-N 0.000 claims 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims 1
- 208000007848 Alcoholism Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 208000022497 Cocaine-Related disease Diseases 0.000 claims 1
- 208000024254 Delusional disease Diseases 0.000 claims 1
- 206010054089 Depressive symptom Diseases 0.000 claims 1
- 206010013654 Drug abuse Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 229930040373 Paraformaldehyde Natural products 0.000 claims 1
- 206010033799 Paralysis Diseases 0.000 claims 1
- 208000019568 Shared Paranoid disease Diseases 0.000 claims 1
- 208000028810 Shared psychotic disease Diseases 0.000 claims 1
- 206010043903 Tobacco abuse Diseases 0.000 claims 1
- 206010044565 Tremor Diseases 0.000 claims 1
- BYPMJBXPNZMNQD-PZJWPPBQSA-N Zicronapine Chemical compound C1C(C)(C)N(C)CCN1[C@H]1C2=CC(Cl)=CC=C2[C@H](C=2C=CC=CC=2)C1 BYPMJBXPNZMNQD-PZJWPPBQSA-N 0.000 claims 1
- 206010001584 alcohol abuse Diseases 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 208000025746 alcohol use disease Diseases 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 201000001272 cocaine abuse Diseases 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002255 enzymatic effect Effects 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 238000004811 liquid chromatography Methods 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
- 230000011987 methylation Effects 0.000 claims 1
- 238000007069 methylation reaction Methods 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 229920002866 paraformaldehyde Polymers 0.000 claims 1
- 208000002851 paranoid schizophrenia Diseases 0.000 claims 1
- -1 phenylmethoxycarbonyl Chemical group 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 230000000698 schizophrenic effect Effects 0.000 claims 1
- 208000019116 sleep disease Diseases 0.000 claims 1
- 201000009032 substance abuse Diseases 0.000 claims 1
- 150000003890 succinate salts Chemical class 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 0 CC1(C)N(*)CCNC1 Chemical compound CC1(C)N(*)CCNC1 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49605803P | 2003-08-18 | 2003-08-18 | |
| US60/496,058 | 2003-08-18 | ||
| DKPA200301180 | 2003-08-18 | ||
| DKPA200301180 | 2003-08-18 | ||
| DKPA200301305 | 2003-09-11 | ||
| DKPA200301305 | 2003-09-11 | ||
| US52024603P | 2003-11-14 | 2003-11-14 | |
| US60/520,246 | 2003-11-14 | ||
| PCT/DK2004/000545 WO2005016900A1 (en) | 2003-08-18 | 2004-08-18 | Succinate and malonate salt of trans-4-(ir,3s)-6-chloro-3-phenylindan-1-yl)-1,2,2-trimethylpiperazine and the use as a medicament |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011154382A Division JP5553802B2 (ja) | 2003-08-18 | 2011-07-13 | トランス−４−（（１ｒ，３ｓ）−６−クロロ−３−フェニルインダン−１−イル）−１，２，２−トリメチルピペラジンのコハク酸塩およびマロン酸塩、および薬剤としての使用方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007502783A JP2007502783A (ja) | 2007-02-15 |
| JP2007502783A5 true JP2007502783A5 (enExample) | 2007-09-27 |
| JP5043429B2 JP5043429B2 (ja) | 2012-10-10 |
Family
ID=34199055
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006523528A Expired - Fee Related JP5043429B2 (ja) | 2003-08-18 | 2004-08-18 | トランス−４−（（１ｒ，３ｓ）−６−クロロ−３−フェニルインダン−１−イル）−１，２，２−トリメチルピペラジンのコハク酸塩およびマロン酸塩、および薬剤としての使用方法 |
| JP2006523529A Expired - Fee Related JP5144930B2 (ja) | 2003-08-18 | 2004-08-18 | トランス−１−（６−クロロ−３−フェニルインダン−１−イル）−３，３−ジメチルピペラジン |
| JP2011154382A Expired - Fee Related JP5553802B2 (ja) | 2003-08-18 | 2011-07-13 | トランス−４−（（１ｒ，３ｓ）−６−クロロ−３−フェニルインダン−１−イル）−１，２，２−トリメチルピペラジンのコハク酸塩およびマロン酸塩、および薬剤としての使用方法 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006523529A Expired - Fee Related JP5144930B2 (ja) | 2003-08-18 | 2004-08-18 | トランス−１−（６−クロロ−３−フェニルインダン−１−イル）−３，３−ジメチルピペラジン |
| JP2011154382A Expired - Fee Related JP5553802B2 (ja) | 2003-08-18 | 2011-07-13 | トランス−４−（（１ｒ，３ｓ）−６−クロロ−３−フェニルインダン−１−イル）−１，２，２−トリメチルピペラジンのコハク酸塩およびマロン酸塩、および薬剤としての使用方法 |
Country Status (15)
| Country | Link |
|---|---|
| US (4) | US7772240B2 (enExample) |
| EP (2) | EP1658276B1 (enExample) |
| JP (3) | JP5043429B2 (enExample) |
| AU (3) | AU2004265022A1 (enExample) |
| BR (2) | BRPI0413595B8 (enExample) |
| CA (2) | CA2536144C (enExample) |
| CY (1) | CY1113039T1 (enExample) |
| HR (2) | HRP20120389T1 (enExample) |
| IL (2) | IL173589A0 (enExample) |
| IS (1) | IS2848B (enExample) |
| MX (2) | MXPA06001938A (enExample) |
| NO (2) | NO332048B1 (enExample) |
| NZ (2) | NZ544715A (enExample) |
| PL (1) | PL1658277T3 (enExample) |
| WO (2) | WO2005016901A1 (enExample) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA014685B1 (ru) | 2003-04-25 | 2010-12-30 | Джилид Сайэнс, Инк. | Фосфонатсодержащие антивирусные соединения (варианты) и фармацевтическая композиция на их основе |
| PL1658277T3 (pl) | 2003-08-18 | 2012-10-31 | H Lundbeck As | Sól bursztynianowa i malonianowa trans-4-((1R,3S)-6-chloro-3-fenyloindan-1-ylo)-1,2,2-tri-metylopiperazyny i zastosowanie jako lek |
| AU2005330489B2 (en) | 2004-07-27 | 2011-08-25 | Gilead Sciences, Inc. | Nucleoside phosphonate conjugates as anti HIV agents |
| WO2006086985A1 (en) * | 2005-02-16 | 2006-08-24 | H. Lundbeck A/S | Tartrate and malate salts of trans-1-((1r,3s)-6-chloro-3-phenylindan-1-yl)-3,3-dimethylpiperazine |
| TWI376373B (en) * | 2005-02-16 | 2012-11-11 | Lundbeck & Co As H | Crystalline base of a pharmaceutical compound |
| TWI453198B (zh) * | 2005-02-16 | 2014-09-21 | Lundbeck & Co As H | 製造反式-1-((1r,3s)-6-氯基-3-苯基茚滿-1-基) -3 , 3 -二甲基六氫吡與其鹽類之方法及製造4-((1r , 3s）-6 -氯基-3-苯基茚滿-1-基 )-1,2,2-三甲基六氫吡與其鹽類之方法 |
| SI2020996T1 (sl) * | 2006-05-16 | 2012-03-30 | Gilead Sciences Inc | Postopek in sestavki za zdravljenje hematološkihmalignosti |
| TW200819426A (en) * | 2006-08-31 | 2008-05-01 | Lundbeck & Co As H | Novel indane compounds |
| CN101657195A (zh) * | 2006-10-06 | 2010-02-24 | 詹森药业有限公司 | 氨基甲酸(s)-(+)-2-(2-氯代苯基)-2-羟基乙酯的新型晶体 |
| KR20090092338A (ko) * | 2006-12-21 | 2009-08-31 | 화이자 프로덕츠 인크. | 2-((4-(1-메틸-4-(피리딘-4-일)-1ｈ-피라졸-3-일)페녹시)메틸)퀴놀린의 숙시네이트 염 |
| CN102065861B (zh) * | 2008-05-07 | 2013-10-16 | H.隆德贝克有限公司 | 反式-4-((1r，3s)-6-氯-3-苯基茚满-1-基)-1，2，2-三甲基哌嗪用于改善认知的用途 |
| US8658617B2 (en) | 2008-07-08 | 2014-02-25 | Gilead Sciences, Inc. | Salts of HIV inhibitor compounds |
| CN102170884A (zh) * | 2008-10-03 | 2011-08-31 | H.隆德贝克有限公司 | 口服制剂 |
| TW201102370A (en) * | 2009-07-07 | 2011-01-16 | Lundbeck & Co As H | Manufacture of 4-((1R,3S)-6-chloro-3-phenyl-indan-1-yl)-1,2,2-trimethyl-piperazine and 1-((1R,3S)-6-chloro-3-phenyl-indan-1-yl)-3,3-dimethyl piperazine |
| EP2399904A1 (en) * | 2010-05-26 | 2011-12-28 | Nabriva Therapeutics AG | Process for the preparation of pleuromutilins |
| EP2639216B1 (en) | 2010-11-09 | 2018-07-11 | Kaneka Corporation | Halogenated indenones and method for producing optically active indanones or optically active indanols by using same |
| US20130331575A1 (en) * | 2011-01-07 | 2013-12-12 | Robert Dancer | Method for resolution of 4-((1R,3S)-6-chloro-3-phenyl-indan-1-yl)-1,2,2-trimethyl-piperazine and 1-((1R,3S)-6-chloro-3-phenyl-indan-1-yl)-3,3-dimethyl-piperazine |
| DK2720989T3 (en) * | 2011-06-20 | 2016-11-28 | H Lundbeck As | Deuterated 1-piperazino-3-phenyl-indanes used to treat schizophrenia |
| TWI552751B (zh) | 2011-06-20 | 2016-10-11 | Ｈ 朗德貝克公司 | 投予４－（（１ｒ，３ｓ）－６－氯－３－苯基－二氫茚－１－基）－１，２，２－三甲基－哌及其鹽用於治療精神分裂症的方法 |
| ES2595240T3 (es) | 2012-07-09 | 2016-12-28 | Lupin Limited | Derivados de tetrahidroquinazolinona como inhibidores de PARP |
| JP2015527365A (ja) | 2012-08-21 | 2015-09-17 | オルソ−クリニカル ダイアグノスティクス，インコーポレイティド | パリペリドンに対する抗体及びその使用 |
| JP6131414B2 (ja) | 2012-08-21 | 2017-05-24 | ヤンセン ファーマシューティカ エヌ．ベー． | アリピプラゾールのハプテン及びイムノアッセイにおけるそれらの使用 |
| ES2691092T3 (es) | 2012-08-21 | 2018-11-23 | Janssen Pharmaceutica Nv | Anticuerpos contra la risperidona y uso de los mismos |
| JP2015529199A (ja) | 2012-08-21 | 2015-10-05 | オルソ−クリニカル ダイアグノスティクス，インコーポレイティド | パリペリドンハプテンに対する抗体及びその使用 |
| CA2882562C (en) | 2012-08-21 | 2019-08-27 | Eric Hryhorenko | Antibodies to aripiprazole and use thereof |
| WO2014031656A1 (en) | 2012-08-21 | 2014-02-27 | Ortho-Clinical Diagnostics, Inc | Antibodies to olanzapine haptens and use thereof |
| JP6389176B2 (ja) | 2012-08-21 | 2018-09-12 | ヤンセン ファーマシューティカ エヌ．ベー． | アリピプラゾールハプテンに対する抗体及びその使用 |
| CA2882596C (en) | 2012-08-21 | 2019-05-14 | Ortho-Clinical Diagnostics, Inc. | Antibodies to olanzapine and use thereof |
| PL2888592T3 (pl) | 2012-08-21 | 2018-03-30 | Janssen Pharmaceutica Nv | Przeciwciała względem kwetiapiny i ich zastosowania |
| JP6450314B2 (ja) | 2012-08-21 | 2019-01-09 | ヤンセン ファーマシューティカ エヌ．ベー． | クエチアピンハプテンに対する抗体及びその使用 |
| EP2888284B1 (en) * | 2012-08-21 | 2022-07-06 | Janssen Pharmaceutica NV | Antibodies to risperidone haptens and use thereof |
| AR094054A1 (es) * | 2012-12-19 | 2015-07-08 | H Lundbeck As | 6-cloro-3-(fenil-d₅)-inden-1-ona y uso de la misma |
| EP3390449A1 (en) | 2015-12-17 | 2018-10-24 | Janssen Pharmaceutica N.V. | Antibodies to risperidone and use thereof |
| US10435478B2 (en) | 2015-12-17 | 2019-10-08 | Janssen Pharmaceutica Nv | Antibodies to quetiapine and use thereof |
| SI3661937T1 (sl) | 2017-08-01 | 2021-11-30 | Gilead Sciences, Inc. | Kristalinične oblike etil((S)-((((2R,5R)-5-(6-amino-9H-purin-9-IL)-4- fluoro-2,5-dihidrofuran-2-IL)oksi)metil)(fenoksi)fosforil)-L-alaninata (GS-9131) za zdravljenje virusnih okužb |
| EP3774742A1 (en) | 2018-04-06 | 2021-02-17 | H. Lundbeck A/S | Process for the preparation of 2,2-dimethylpiperazine |
| WO2020089147A1 (en) | 2018-10-29 | 2020-05-07 | H. Lundbeck A/S | Amorphous compounds of formula (i) and amorphous compounds of formula (i) salts |
| WO2020114853A1 (en) | 2018-12-03 | 2020-06-11 | H. Lundbeck A/S | Prodrugs of 4-((1r,3s)-6-chloro-3-phenyl-2,3-dihydro-1h-inden-1-yl)-1,2,2-trimethylpiperazine and 4-((1/r,3s)-6-chloro-3-(phenyl-d5)-2,3-dihydro-1h-inden-1-yl)-2,2-dimethy-1-(methyl-d3)piperazine |
| US11358934B2 (en) | 2020-03-23 | 2022-06-14 | Caamtech, Inc. | Crystalline forms of psilacetin |
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| CA2132411A1 (en) * | 1994-09-19 | 1996-03-20 | Michael Trani | Enzymatic esterification of long-chain racemic acids and alcohols |
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| US6455736B1 (en) * | 1994-12-16 | 2002-09-24 | Uop Llc | Process for preparation of pharmaceutically desired sertraline and sertraline analogs |
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| US6268367B1 (en) * | 1998-02-23 | 2001-07-31 | Zymogenetics, Inc. | Piperazine derivatives for treating bone deficit conditions |
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| KR100605140B1 (ko) * | 1998-05-22 | 2006-07-28 | 싸이오스 인크 | 심장병 및 다른 질병을 치료하기 위한 헤테로 고리 화합물및 그 치료 방법 |
| DE19824470A1 (de) | 1998-05-30 | 1999-12-02 | Boehringer Ingelheim Pharma | Neue Neurokininantagonisten, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen |
| GB9818916D0 (en) | 1998-08-28 | 1998-10-21 | Smithkline Beecham Plc | Use |
| FR2786769B1 (fr) | 1998-12-04 | 2002-10-25 | Synthelabo | Derives de 2,5-diazabicyclo[2.2.1]heptane, leur preparation et leur application en therapeutique |
| JP2000351773A (ja) * | 1999-06-08 | 2000-12-19 | Yamanouchi Pharmaceut Co Ltd | フラン誘導体からなる医薬 |
| EP1059302A1 (en) | 1999-06-08 | 2000-12-13 | Aventis Pharma Deutschland GmbH | Factor VIIa inhibitors |
| AR031520A1 (es) | 1999-06-11 | 2003-09-24 | Vertex Pharma | Un compuesto inhibidor de aspartilo proteasa, una composicion que lo comprende y un metodo para tratar un paciente con dicha composicion |
| US6369226B1 (en) * | 1999-06-21 | 2002-04-09 | Agouron Pharmaceuticals, Inc. | Substituted benzamide inhibitors of rhinovirus 3C protease |
| IN187170B (enExample) | 2000-01-04 | 2002-02-23 | Sun Pharmaceutical Ind Ltd | |
| PL1658277T3 (pl) | 2003-08-18 | 2012-10-31 | H Lundbeck As | Sól bursztynianowa i malonianowa trans-4-((1R,3S)-6-chloro-3-fenyloindan-1-ylo)-1,2,2-tri-metylopiperazyny i zastosowanie jako lek |
| WO2006086985A1 (en) | 2005-02-16 | 2006-08-24 | H. Lundbeck A/S | Tartrate and malate salts of trans-1-((1r,3s)-6-chloro-3-phenylindan-1-yl)-3,3-dimethylpiperazine |
| TWI453198B (zh) | 2005-02-16 | 2014-09-21 | Lundbeck & Co As H | 製造反式-1-((1r,3s)-6-氯基-3-苯基茚滿-1-基) -3 , 3 -二甲基六氫吡與其鹽類之方法及製造4-((1r , 3s）-6 -氯基-3-苯基茚滿-1-基 )-1,2,2-三甲基六氫吡與其鹽類之方法 |
| TWI376373B (en) | 2005-02-16 | 2012-11-11 | Lundbeck & Co As H | Crystalline base of a pharmaceutical compound |
-
2004
- 2004-08-18 PL PL04762772T patent/PL1658277T3/pl unknown
- 2004-08-18 WO PCT/DK2004/000546 patent/WO2005016901A1/en not_active Ceased
- 2004-08-18 MX MXPA06001938A patent/MXPA06001938A/es not_active Application Discontinuation
- 2004-08-18 WO PCT/DK2004/000545 patent/WO2005016900A1/en not_active Ceased
- 2004-08-18 BR BRPI0413595A patent/BRPI0413595B8/pt not_active IP Right Cessation
- 2004-08-18 US US10/568,292 patent/US7772240B2/en not_active Expired - Fee Related
- 2004-08-18 HR HRP20120389TT patent/HRP20120389T1/hr unknown
- 2004-08-18 JP JP2006523528A patent/JP5043429B2/ja not_active Expired - Fee Related
- 2004-08-18 US US10/568,572 patent/US7767683B2/en not_active Expired - Lifetime
- 2004-08-18 AU AU2004265022A patent/AU2004265022A1/en not_active Abandoned
- 2004-08-18 MX MXPA06001838A patent/MXPA06001838A/es active IP Right Grant
- 2004-08-18 EP EP04739041A patent/EP1658276B1/en not_active Expired - Lifetime
- 2004-08-18 NZ NZ544715A patent/NZ544715A/en not_active IP Right Cessation
- 2004-08-18 AU AU2004265021A patent/AU2004265021B2/en not_active Ceased
- 2004-08-18 CA CA2536144A patent/CA2536144C/en not_active Expired - Fee Related
- 2004-08-18 EP EP04762772A patent/EP1658277B1/en not_active Expired - Lifetime
- 2004-08-18 BR BRPI0413555-5A patent/BRPI0413555A/pt not_active IP Right Cessation
- 2004-08-18 HR HRP20121010TT patent/HRP20121010T1/hr unknown
- 2004-08-18 JP JP2006523529A patent/JP5144930B2/ja not_active Expired - Fee Related
- 2004-08-18 NZ NZ575575A patent/NZ575575A/en not_active IP Right Cessation
- 2004-08-18 CA CA002536073A patent/CA2536073A1/en not_active Abandoned
-
2006
- 2006-01-26 IS IS8265A patent/IS2848B/is unknown
- 2006-02-07 IL IL173589A patent/IL173589A0/en unknown
- 2006-02-16 IL IL173788A patent/IL173788A/en unknown
- 2006-03-10 NO NO20061151A patent/NO332048B1/no not_active IP Right Cessation
- 2006-03-10 NO NO20061153A patent/NO20061153L/no unknown
-
2010
- 2010-06-22 US US12/820,392 patent/US8227607B2/en not_active Expired - Fee Related
- 2010-07-30 AU AU2010206058A patent/AU2010206058C1/en not_active Ceased
- 2010-11-04 US US12/939,904 patent/US8076342B2/en not_active Expired - Fee Related
-
2011
- 2011-07-13 JP JP2011154382A patent/JP5553802B2/ja not_active Expired - Fee Related
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2012
- 2012-05-24 CY CY20121100469T patent/CY1113039T1/el unknown
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