UA79248C2 - Mandelate salts of substituted tetracyclic tetrahydrofuran derivatives - Google Patents
Mandelate salts of substituted tetracyclic tetrahydrofuran derivatives Download PDFInfo
- Publication number
- UA79248C2 UA79248C2 UA20040604168A UA20040604168A UA79248C2 UA 79248 C2 UA79248 C2 UA 79248C2 UA 20040604168 A UA20040604168 A UA 20040604168A UA 20040604168 A UA20040604168 A UA 20040604168A UA 79248 C2 UA79248 C2 UA 79248C2
- Authority
- UA
- Ukraine
- Prior art keywords
- mandelic acid
- acid salt
- formula
- tetrahydro
- cyclohepta
- Prior art date
Links
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 title abstract description 13
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical class [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 title abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 60
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical class O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 23
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 208000028017 Psychotic disease Diseases 0.000 claims description 5
- 206010013663 drug dependence Diseases 0.000 claims description 5
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- 230000036506 anxiety Effects 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical class OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims description 4
- 229960002510 mandelic acid Drugs 0.000 claims description 4
- 206010027599 migraine Diseases 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- 208000019116 sleep disease Diseases 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 239000002178 crystalline material Substances 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims 2
- 238000000746 purification Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 20
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 abstract description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract description 2
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- 239000000543 intermediate Substances 0.000 description 36
- 238000000034 method Methods 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 9
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
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- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Addiction (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01204465 | 2001-11-09 | ||
| PCT/EP2002/011136 WO2003040122A1 (en) | 2001-11-09 | 2002-11-08 | Novel mandelate salts of substituted tetracyclic tetrahydrofuran derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA79248C2 true UA79248C2 (en) | 2007-06-11 |
Family
ID=8181272
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20040604168A UA79248C2 (en) | 2001-11-09 | 2002-08-11 | Mandelate salts of substituted tetracyclic tetrahydrofuran derivatives |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US7317115B2 (pt) |
| EP (1) | EP1446397B1 (pt) |
| JP (1) | JP2005508988A (pt) |
| KR (1) | KR100962325B1 (pt) |
| CN (1) | CN1582282B (pt) |
| AR (1) | AR037285A1 (pt) |
| AT (1) | ATE299138T1 (pt) |
| AU (1) | AU2002349327B2 (pt) |
| BR (1) | BR0212770A (pt) |
| CA (1) | CA2465043C (pt) |
| DE (1) | DE60204982T2 (pt) |
| EA (1) | EA006980B1 (pt) |
| ES (1) | ES2244818T3 (pt) |
| HR (1) | HRP20040395A2 (pt) |
| HU (1) | HUP0402224A3 (pt) |
| IL (2) | IL161866A0 (pt) |
| MX (1) | MXPA04004365A (pt) |
| MY (1) | MY128237A (pt) |
| NO (1) | NO328548B1 (pt) |
| NZ (1) | NZ531739A (pt) |
| PL (1) | PL368456A1 (pt) |
| TW (1) | TW200407117A (pt) |
| UA (1) | UA79248C2 (pt) |
| WO (1) | WO2003040122A1 (pt) |
| ZA (1) | ZA200403454B (pt) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6998494B2 (en) * | 2001-12-07 | 2006-02-14 | Janssen Pharmaceutica N.V. | Preparation of trans-fused 3,3a,8,12b-tetrahydro-2h-dibenzo[3,4:6,7]cyclohepta[1,2-b]furan derivatives |
| WO2005013969A1 (en) * | 2003-07-15 | 2005-02-17 | Janssen Pharmaceutica N.V. | Antipsychotic agent with socializing properties |
| AU2005313325C1 (en) | 2004-12-07 | 2011-11-10 | Janssen Pharmaceutica N.V. | Substituted tetracyclic tetrahydrofuran, pyrrolidine and tetrahydrothiophene derivatives |
| CN101107254B (zh) | 2005-01-27 | 2010-12-08 | 詹森药业有限公司 | 在中枢神经系统病症的治疗中作为5ht2抑制剂的杂环四环四氢呋喃衍生物 |
| WO2006134163A2 (en) | 2005-06-17 | 2006-12-21 | Janssen Pharmaceutica N.V. | Novel tetracyclic tetrahydrofuran derivatives containing a cyclic amine side chain |
| US8507040B2 (en) | 2008-05-08 | 2013-08-13 | Air Products And Chemicals, Inc. | Binary and ternary metal chalcogenide materials and method of making and using same |
| US8765223B2 (en) * | 2008-05-08 | 2014-07-01 | Air Products And Chemicals, Inc. | Binary and ternary metal chalcogenide materials and method of making and using same |
| US8962675B1 (en) * | 2013-09-12 | 2015-02-24 | Abbvie Inc. | Atrasentan mandelate salts |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3644462A1 (de) | 1986-12-24 | 1988-07-07 | Basf Ag | Verfahren zur herstellung von 5h-dibenzo(a,d)cyclohepten-5-onen |
| JP2656720B2 (ja) * | 1992-12-09 | 1997-09-24 | 武田薬品工業株式会社 | 光学活性アミノクマラン誘導体 |
| AU1945495A (en) * | 1994-03-16 | 1995-10-03 | Novo Nordisk A/S | Acid addition salts of 2,3,4,5-tetrahydro-1h-3-benzazepine compounds |
| JP3199751B2 (ja) * | 1996-04-12 | 2001-08-20 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 置換された四環式テトラヒドロフラン誘導体 |
| EE03902B1 (et) | 1996-05-20 | 2002-12-16 | Janssen Pharmaceutica N.V. | Osakesed, nende valmistamismeetod ja kasutamine, farmatseutiline doseerimisvorm ja selle valmistamismeetod, tahke dispersioon ning farmatseutiline pakend |
| UA52778C2 (uk) * | 1997-10-10 | 2003-01-15 | Янссен Фармацевтика Н.В. | Галогенозаміщені тетрациклічні похідні тетрагідрофурану, спосіб їх отримання та композиція на їх основі |
| US6281247B1 (en) * | 1998-03-03 | 2001-08-28 | Novo Nordisk A/S | Salt forms of (2E)-5-amino-5-methylhex-2-enoic acid N-methyl-N-((1R)-1-(N-methyl-N-((1R)-1-(methylcarbamoyl)-2-phenylethyl)carbamoyl)-2-(2-naphthyl)ethyl)amide |
| HUP9904624A2 (hu) * | 1999-12-17 | 2002-01-28 | Sanofi-Synthelabo | Szacharinszármazékok, eljárás előállításukra, az ezeket tartalmazó gyógyszerkészítmények és intermedierjeik |
| EP1186303A3 (en) * | 2000-09-06 | 2003-12-10 | Pfizer Products Inc. | Pharmaceutical combinations, for the treatment of stroke and traumatic brain injury, containing a neutrophil inhibiting factor and an selective NMDA-NR2B receptor antagonist |
-
2002
- 2002-08-11 UA UA20040604168A patent/UA79248C2/uk unknown
- 2002-11-07 MY MYPI20024166A patent/MY128237A/en unknown
- 2002-11-08 NZ NZ531739A patent/NZ531739A/en not_active IP Right Cessation
- 2002-11-08 AR ARP020104298A patent/AR037285A1/es unknown
- 2002-11-08 AU AU2002349327A patent/AU2002349327B2/en not_active Ceased
- 2002-11-08 MX MXPA04004365A patent/MXPA04004365A/es active IP Right Grant
- 2002-11-08 TW TW091132840A patent/TW200407117A/zh unknown
- 2002-11-08 US US10/491,799 patent/US7317115B2/en not_active Expired - Fee Related
- 2002-11-08 CA CA2465043A patent/CA2465043C/en not_active Expired - Fee Related
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- 2002-11-08 KR KR1020047002379A patent/KR100962325B1/ko not_active IP Right Cessation
- 2002-11-08 AT AT02781214T patent/ATE299138T1/de not_active IP Right Cessation
- 2002-11-08 PL PL02368456A patent/PL368456A1/xx unknown
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- 2002-11-08 HU HU0402224A patent/HUP0402224A3/hu unknown
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