HRP20110645T1 - Kristalična baza trans-1-((1r,3s)-6-kloro-3-fenilindan-1-il)-3,3-dimetilpiperazina - Google Patents
Kristalična baza trans-1-((1r,3s)-6-kloro-3-fenilindan-1-il)-3,3-dimetilpiperazina Download PDFInfo
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- HRP20110645T1 HRP20110645T1 HR20110645T HRP20110645T HRP20110645T1 HR P20110645 T1 HRP20110645 T1 HR P20110645T1 HR 20110645 T HR20110645 T HR 20110645T HR P20110645 T HRP20110645 T HR P20110645T HR P20110645 T1 HRP20110645 T1 HR P20110645T1
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- 239000012971 dimethylpiperazine Substances 0.000 title claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims abstract 28
- 230000005855 radiation Effects 0.000 claims abstract 2
- 239000002585 base Substances 0.000 claims 22
- 238000000034 method Methods 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 8
- 239000003814 drug Substances 0.000 claims 6
- 238000002360 preparation method Methods 0.000 claims 6
- 208000028017 Psychotic disease Diseases 0.000 claims 5
- 239000012458 free base Substances 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 201000000980 schizophrenia Diseases 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- 206010012335 Dependence Diseases 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 208000024891 symptom Diseases 0.000 claims 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 2
- 208000019022 Mood disease Diseases 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- 208000017194 Affective disease Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 208000021465 Brief psychotic disease Diseases 0.000 claims 1
- 208000024254 Delusional disease Diseases 0.000 claims 1
- 206010054089 Depressive symptom Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims 1
- 206010026749 Mania Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000020186 Schizophreniform disease Diseases 0.000 claims 1
- 229960003920 cocaine Drugs 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 claims 1
- 238000004128 high performance liquid chromatography Methods 0.000 claims 1
- 230000001035 methylating effect Effects 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 239000003176 neuroleptic agent Substances 0.000 claims 1
- 230000000701 neuroleptic effect Effects 0.000 claims 1
- 229960002715 nicotine Drugs 0.000 claims 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 1
- 208000002851 paranoid schizophrenia Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 208000022610 schizoaffective disease Diseases 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 208000019116 sleep disease Diseases 0.000 claims 1
- 150000003890 succinate salts Chemical group 0.000 claims 1
- 238000000634 powder X-ray diffraction Methods 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
- C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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
-
- 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
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
-
- 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
-
- 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
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Kristalična baza spoja formule (I), Spoj I, trans-1-((1R,3S)-6-kloro-3-fenilindan-1-il)-3,3-dimetilpiperazin, naznačena time što difraktogram rendgenskog zračenja praška, dobiven uporabom CuK?1 zračenja (λ=1.5406 ?), ima vrhove pri sljedećim 2θ-kutevima: 6.1, 11.1, 12.1, 16.2, 16.8, 18.3, 18.6, 20.0. Patent sadrži još 33 patentna zahtjeva.
Claims (34)
1. Kristalična baza spoja formule (I), Spoj I, trans-1-((1R,3S)-6-kloro-3-fenilindan-1-il)-3,3-dimetilpiperazin,
[image]
naznačena time što difraktogram rendgenskog zračenja praška, dobiven uporabom CuKα1 zračenja (λ=1.5406 Å), ima vrhove pri sljedećim 2θ-kutevima: 6.1, 11.1, 12.1, 16.2, 16.8, 18.3, 18.6, 20.0.
2. Kristalična baza prema zahtjevu 1, naznačena time što ima DSC termogram koji odgovara onome na Slici 2.
3. Kristalična baza prema zahtjevu 1 ili 2, naznačena time što ima DSC trag koji pokazuje endotermu s početkom na oko 91-.
4. Kristalična baza prema bilo kojem od zahtjeva 1- koja je bezvodna.
5. Kristalična baza prema zahtjevu 4, koja je bez otapala.
6. Kristalična baza prema bilo kojem od zahtjeva 1-5, ima čistoću od najmanje 98% mjereno HPLC-om (područje).
7. Kristalična baza prema bilo kojem od zahtjeva 1-6, gdje je enantiomerni suvišak Spoja I najmanje 98%.
8. Kristalična baza prema bilo kojem od zahtjeva 1-7 za uporabu u medicini.
9. Farmaceutska smjesa koja sadrži kristaličnu bazu prema bilo kojem od zahtjeva 1-7.
10. Uporaba kristalične baze prema bilo kojem od zahtjeva 1-7 za pripremu lijeka za liječenje bolesti izabrane iz skupine koja obuhvaća: bolesti koje uključuju psihotične simptome, shizofreniju, anksiozne poremećaje, afektivne poremećaje, poremećaje spavanja, migrenu, neuroleptički induciranu Parkinsonovu bolest i ovisnosti.
11. Uporaba prema zahtjevu 10, gdje je afektivni poremećaj depresija.
12. Uporaba prema zahtjevu 10, gdje ovisnost može biti ovisnost o kokainu, nikotinu ili alkoholu.
13. Uporaba prema zahtjevu 10 za pripremu lijeka za liječenje shizofrenije ili drugih psihotičnih poremećaja.
14. Uporaba prema zahtjevu 13 za pripremu lijeka za liječenje jednog ili više pozitivnih simptoma, negativnih simptoma i depresivnih simptoma shizofrenije.
15. Uporaba kristalične baze prema bilo kojem od zahtjeva 1-7 za pripremu lijeka za liječenje bolesti izabrane iz skupine koja obuhvaća: shizofreniju, shizofreniformni poremećaj, shizoafektivni poremećaj, deluzijski poremećaj, kratki psihotični poremećaj, podijeljeni psihotični poremećaj te maniju i bipolarni poremećaj.
16. Uporaba prema bilo kojem od zahtjeva 10-15, pri čemu je liječeni bolesnik također na liječenju s barem jednim drugim lijekom.
17. Postupak pripreme kristalične baze Spoja I kako je definiran u zahtjevu 1, naznačen time što kristalični Spoj I nastaje u otapalu.
18. Postupak prema zahtjevu 17, gdje je spomenuto otapalo etil acetat ili heptan ili njihova smjesa.
19. Postupak prema zahtjevu 17 ili obuhvaća kristalizaciju pomoću taloženja baze Spoja I iz otapala, i odvajanje otapala od dobivene kristalične baze Spoja I.
20. Postupak prema bilo kojem od zahtjeva 17-19, gdje je kristalična baza Spoja I kako je definirano u bilo kojem od zahtjeva 2-7.
21. Kristalična baza Spoja I koja se može dobiti postupkom prema bilo kojem od zahtjeva 17-19.
22. Postupak proizvodnje Spoja I čija je formula definirana u zahtjevu obuhvaća korak gdje se Spoj I pretvara u kristaličnu slobodnu bazu Spoja I.
23. Postupak prema zahtjevu 22, dalje obuhvaća pretvorbu kristalične baze Spoja I u sol Spoja I.
24. Postupak prema zahtjevu 23, naznačen time što se baza Spoja I oslobađa i taloži u kristaličnom obliku i zatim pretvara u sol Spoja I.
25. Postupak prema zahtjevu 24, gdje se istaložena baza Spoja I u kristaličnom obliku ponovno kristalizira jednom ili više puta prije pretvaranja u sol Spoja I.
26. Postupak prema zahtjevu 24 ili 25, gdje se spomenuta baza Spoja I oslobađa od sirove soli ili sirove smjese Spoja I.
27. Postupak prema bilo kojem od zahtjeva 22-26, gdje se kristalična baza Spoja I dobiva prema postupku iz zahtjeva 17 ili 18.
28. Postupak prema bilo kojem od zahtjeva 22-27, koji dalje obuhvaća izradu farmaceutske smjese koja sadrži Spoj I ili njegovu sol.
29. Postupak prema bilo kojem od zahtjeva 22-27, koji dalje obuhvaća korak metilacije Spoja I na sekundarnom aminu tako da se dobije slobodna baza spoja formule II:
[image]
30. Postupak prema zahtjevu 29, gdje se spoj formule II taloži kao sol.
31. Postupak prema zahtjevu 30, gdje je spomenuta sol sukcinat ili malonat Spoja II.
32. Postupak prema bilo kojem od zahtjeva 29-31, koji dalje obuhvaća izradu farmaceutske smjese koja sadrži Spoj II ili njegovu sol.
33. Slobodna baza spoja formule (I) [Spoj I, trans-1-((1R,3S)-6-kloro-3-fenilindan-1-il)-3,3-dimetilpiperazinie] kako je definirano u zahtjevu 1, u krutom obliku.
34. Slobodna baza prema zahtjevu 33, gdje spomenuta krutina sadrži kristaličnu bazu Spoja I.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65341905P | 2005-02-16 | 2005-02-16 | |
| DKPA200500239 | 2005-02-16 | ||
| PCT/DK2006/000088 WO2006086986A1 (en) | 2005-02-16 | 2006-02-14 | Crystalline base of trans-1-((1r,3s)-6-chloro-3-phenylindan-1-yl)-3,3-dimethylpiperazine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110645T1 true HRP20110645T1 (hr) | 2011-10-31 |
Family
ID=37908539
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20110645T HRP20110645T1 (hr) | 2005-02-16 | 2011-09-07 | Kristalična baza trans-1-((1r,3s)-6-kloro-3-fenilindan-1-il)-3,3-dimetilpiperazina |
Country Status (29)
| Country | Link |
|---|---|
| US (2) | US7648991B2 (hr) |
| EP (1) | EP1853576B1 (hr) |
| JP (1) | JP5055135B2 (hr) |
| KR (1) | KR101386387B1 (hr) |
| CN (1) | CN101119983B (hr) |
| AR (1) | AR052909A1 (hr) |
| AT (1) | ATE515501T1 (hr) |
| AU (1) | AU2006215957B9 (hr) |
| BR (1) | BRPI0607436B8 (hr) |
| CA (1) | CA2597622C (hr) |
| CY (1) | CY1111857T1 (hr) |
| DK (1) | DK1853576T3 (hr) |
| EA (1) | EA017631B1 (hr) |
| ES (1) | ES2368786T3 (hr) |
| HK (1) | HK1117525A1 (hr) |
| HR (1) | HRP20110645T1 (hr) |
| IL (1) | IL184551A (hr) |
| MX (1) | MX2007009980A (hr) |
| MY (1) | MY148683A (hr) |
| NO (1) | NO339863B1 (hr) |
| NZ (1) | NZ556397A (hr) |
| PL (1) | PL1853576T3 (hr) |
| PT (1) | PT1853576E (hr) |
| RS (1) | RS51944B (hr) |
| SI (1) | SI1853576T1 (hr) |
| TW (1) | TWI376373B (hr) |
| UA (1) | UA95901C2 (hr) |
| WO (1) | WO2006086986A1 (hr) |
| ZA (1) | ZA200705982B (hr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2004265021B2 (en) * | 2003-08-18 | 2010-05-27 | H. Lundbeck A/S | 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 |
| 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 |
| WO2009135495A1 (en) * | 2008-05-07 | 2009-11-12 | H. Lundbeck A/S | Method for treating cognitive deficits |
| EP2344163A1 (en) * | 2008-10-03 | 2011-07-20 | H. Lundbeck A/S | Oral formulation |
| LT2720989T (lt) * | 2011-06-20 | 2016-11-25 | H. Lundbeck A/S | Deuterinti 1-piperazin-3-fenilindanai, skirti šizofrenijos gydymui |
| US20210395208A1 (en) | 2018-10-29 | 2021-12-23 | H. Lundeck 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4031216A (en) | 1974-08-12 | 1977-06-21 | Knoll A.G. Chemische Fabriken | 3-(3,4-Dialkoxy-benzyl)-3-methyl-piperazines |
| IE50867B1 (en) | 1980-02-29 | 1986-08-06 | Kefalas As | Indane derivatives |
| DE3139970A1 (de) | 1981-10-08 | 1983-04-28 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue carbonsaeurederivate, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel |
| US5026853A (en) | 1987-04-01 | 1991-06-25 | Janssen Pharmaceutica N.V. | 4-substituted-2(or 3)aminocarbonyl-1-piperazineacetamide |
| US5466806A (en) | 1989-02-08 | 1995-11-14 | Biochem Pharma Inc. | Processes for preparing substituted 1,3-oxathiolanes with antiviral properties |
| CZ287406B6 (cs) | 1991-11-05 | 2000-11-15 | Smithkline Beecham Corporation | Indanové a indenové deriváty, způsob jejich výroby a farmaceutické prostředky s jejich obsahem |
| CA2091204C (en) | 1992-03-11 | 1997-04-08 | Ronald J. Mattson | Antiischemic-piperazinyl and piperidinyl-cyclohexanes |
| DK55192D0 (da) | 1992-04-28 | 1992-04-28 | Lundbeck & Co As H | 1-piperazino-1,2-dihydroindenderivater |
| JPH06184132A (ja) | 1992-12-22 | 1994-07-05 | Kotobuki Seiyaku Kk | ベンゾフラン誘導体及びその製造方法並びに尿酸排泄剤 |
| CA2176500C (en) | 1993-11-30 | 1999-09-28 | George J. Quallich | Process for preparing a chiral tetralone |
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