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 |
|---|---|---|---|
| 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 |
| 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 |
| 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 Before (1)
| 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 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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) | US7767683B2 (enExample) |
| EP (2) | EP1658277B1 (enExample) |
| JP (3) | JP5144930B2 (enExample) |
| AU (3) | AU2004265022A1 (enExample) |
| BR (2) | BRPI0413595B8 (enExample) |
| CA (2) | CA2536073A1 (enExample) |
| CY (1) | CY1113039T1 (enExample) |
| HR (2) | HRP20120389T1 (enExample) |
| IL (2) | IL173589A0 (enExample) |
| IS (1) | IS2848B (enExample) |
| MX (2) | MXPA06001838A (enExample) |
| NO (2) | NO20061153L (enExample) |
| NZ (2) | NZ575575A (enExample) |
| PL (1) | PL1658277T3 (enExample) |
| WO (2) | WO2005016901A1 (enExample) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1628685T3 (da) | 2003-04-25 | 2011-03-21 | Gilead Sciences Inc | Antivirale phosphonatanaloge |
| WO2005016901A1 (en) * | 2003-08-18 | 2005-02-24 | H. Lundbeck A/S | Trans-1(6-chloro-3-phenylindan-1-yl)-3,3-dimethylpiperazine |
| AU2005330489B2 (en) | 2004-07-27 | 2011-08-25 | Gilead Sciences, Inc. | Nucleoside phosphonate conjugates as anti HIV agents |
| TWI376373B (en) * | 2005-02-16 | 2012-11-11 | Lundbeck & Co As H | Crystalline base of a pharmaceutical compound |
| 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 |
| KR101424832B1 (ko) * | 2006-05-16 | 2014-08-06 | 길리애드 사이언시즈, 인코포레이티드 | 악성 혈액 종양 치료 방법 및 악성 혈액 종양 치료용 조성물 |
| TW200819426A (en) * | 2006-08-31 | 2008-05-01 | Lundbeck & Co As H | Novel indane compounds |
| WO2008045391A2 (en) | 2006-10-06 | 2008-04-17 | Janssen Pharmaceutica Nv | Novel crystal of (s)-(+)-2-(2-chlorophenyl)-2-hydroxy-ethyl carbamate |
| PT2125786E (pt) * | 2006-12-21 | 2011-04-21 | Pfizer Prod Inc | Sal succinato de 2-((4-(1-metil-4-(piridin-4-il)-1hpirazol- 3-il)fenoxi)metil)quinolina |
| MX2010012037A (es) * | 2008-05-07 | 2010-11-30 | Lundbeck & Co As H | Composiciones y uso utiles para tratar trastornos cognitivos. |
| PE20110219A1 (es) | 2008-07-08 | 2011-03-31 | Gilead Sciences Inc | Sales del compuesto n-[(s)({[(2r,5r)-5-(6-amino-9h-purin-9-il)-4-fluoro-2,5-dihidrofuran-2-il]oxi}metil)fenoxifosfinoil]-l-alaninato de etilo como inhibidores de vih |
| AU2009298264A1 (en) * | 2008-10-03 | 2010-04-08 | H. Lundbeck A/S | Oral formulation |
| 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 |
| WO2012063843A1 (ja) | 2010-11-09 | 2012-05-18 | 株式会社カネカ | ハロゲン化インデノン類及びそれを用いた光学活性インダノン類又は光学活性インダノール類の製造方法 |
| AU2012204839A1 (en) | 2011-01-07 | 2013-08-22 | H. Lundbeck A/S | 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 |
| EA024651B1 (ru) * | 2011-06-20 | 2016-10-31 | Х. Лундбекк А/С | Дейтерированные 1-пиперазино-3-фенилинданы, применяемые для лечения шизофрении |
| JO3421B1 (ar) | 2011-06-20 | 2019-10-20 | H Lundbeck As | طريقة لإعطاء 1-((1ار.3س)-6-كلورو-3-فينيل-اندان-1-ايل)-1.2.2-ترايميثيل- بيبيرازين واملاجها لمعالجة انفصام الشخصية |
| CA2877826C (en) | 2012-07-09 | 2016-08-16 | Lupin Limited | Tetrahydroquinazolinone derivatives as parp inhibitors |
| CA2882615C (en) | 2012-08-21 | 2019-07-09 | Ortho-Clinical Diagnostics, Inc. | Antibodies to quetiapine and use thereof |
| EP2888284B1 (en) | 2012-08-21 | 2022-07-06 | Janssen Pharmaceutica NV | Antibodies to risperidone haptens and use thereof |
| CN107253993B (zh) | 2012-08-21 | 2021-10-22 | 詹森药业有限公司 | 奥氮平的抗体及其用途 |
| ES2870004T3 (es) | 2012-08-21 | 2021-10-26 | Janssen Pharmaceutica Nv | Anticuerpos contra la risperidona y uso de los mismos |
| ES2762105T3 (es) | 2012-08-21 | 2020-05-22 | Janssen Pharmaceutica Nv | Anticuerpos para aripiprazol y uso de los mismos |
| ES2788716T3 (es) | 2012-08-21 | 2020-10-22 | Janssen Pharmaceutica Nv | Anticuerpos para haptenos de quetiapina y uso de los mismos |
| EP2888285B1 (en) | 2012-08-21 | 2024-04-17 | Janssen Pharmaceutica NV | Antibodies to aripiprazole haptens and use thereof |
| HK1211958A1 (en) | 2012-08-21 | 2016-06-03 | Ortho-Clinical Diagnostics, Inc. | Antibodies to paliperidone and use thereof |
| CN104736566A (zh) | 2012-08-21 | 2015-06-24 | 奥索临床诊断有限公司 | 帕潘立酮半抗原的抗体及其用途 |
| TR201910347T4 (tr) | 2012-08-21 | 2019-07-22 | Janssen Pharmaceutica Nv | Olanzapin haptenlerine yönelik antikorlar ve bunların kullanımı. |
| WO2014031584A1 (en) | 2012-08-21 | 2014-02-27 | Janssen Pharmaceutica Nv | Haptens of aripiprazole and their use in immunoassays |
| AR094054A1 (es) * | 2012-12-19 | 2015-07-08 | H Lundbeck As | 6-cloro-3-(fenil-d₅)-inden-1-ona y uso de la misma |
| JP6994461B2 (ja) | 2015-12-17 | 2022-02-04 | ヤンセン ファーマシューティカ エヌ．ベー． | クエチアピンに対する抗体及びその使用 |
| CA3008809A1 (en) | 2015-12-17 | 2017-06-22 | Janssen Pharmaceutica Nv | Antibodies to risperidone and use thereof |
| ES2969496T3 (es) | 2017-08-01 | 2024-05-20 | Gilead Sciences Inc | Formas cristalinas de ((S)-((((2R,5R)-5-(6-amino-9H-purin-9-il)-4-fluoro-2,5-dihidrofuran-2- il)oxi)metil)(fenoxi)fosforil)-L-alaninato de etilo para tratar infecciones virales |
| MA52183A (fr) | 2018-04-06 | 2021-02-17 | H Lundbeck As | Procédé de préparation de 2,2-diméthylpipérazine |
| US20210395208A1 (en) | 2018-10-29 | 2021-12-23 | H. Lundeck A/S | Amorphous compounds of formula (i) and amorphous compounds of formula (i) salts |
| EP3891134A1 (en) * | 2018-12-03 | 2021-10-13 | 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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| US6410794B1 (en) | 1994-12-16 | 2002-06-25 | Uop Llc | Process for preparation of pharmaceutically desired chiral tetralone from tetralones |
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| GB9818916D0 (en) | 1998-08-28 | 1998-10-21 | Smithkline Beecham Plc | Use |
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| 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 | |
| WO2005016901A1 (en) * | 2003-08-18 | 2005-02-24 | H. Lundbeck A/S | Trans-1(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 |
| 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 |
-
2004
- 2004-08-18 WO PCT/DK2004/000546 patent/WO2005016901A1/en not_active Ceased
- 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 CA CA002536073A patent/CA2536073A1/en not_active Abandoned
- 2004-08-18 NZ NZ575575A patent/NZ575575A/en not_active IP Right Cessation
- 2004-08-18 BR BRPI0413555-5A patent/BRPI0413555A/pt not_active IP Right Cessation
- 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 EP04762772A patent/EP1658277B1/en not_active Expired - Lifetime
- 2004-08-18 US US10/568,572 patent/US7767683B2/en active Active
- 2004-08-18 AU AU2004265021A patent/AU2004265021B2/en not_active Ceased
- 2004-08-18 JP JP2006523529A patent/JP5144930B2/ja not_active Expired - Fee Related
- 2004-08-18 HR HRP20120389TT patent/HRP20120389T1/hr unknown
- 2004-08-18 NZ NZ544715A patent/NZ544715A/en not_active IP Right Cessation
- 2004-08-18 HR HRP20121010TT patent/HRP20121010T1/hr unknown
- 2004-08-18 PL PL04762772T patent/PL1658277T3/pl unknown
- 2004-08-18 JP JP2006523528A patent/JP5043429B2/ja not_active Expired - Fee Related
- 2004-08-18 US US10/568,292 patent/US7772240B2/en not_active Expired - Fee Related
- 2004-08-18 EP EP04739041A patent/EP1658276B1/en not_active Expired - Lifetime
- 2004-08-18 MX MXPA06001938A patent/MXPA06001938A/es not_active Application Discontinuation
- 2004-08-18 CA CA2536144A patent/CA2536144C/en not_active Expired - Fee Related
-
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 NO20061153A patent/NO20061153L/no unknown
- 2006-03-10 NO NO20061151A patent/NO332048B1/no not_active IP Right Cessation
-
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
-
2012
- 2012-05-24 CY CY20121100469T patent/CY1113039T1/el unknown
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