AU725756B2 - New 2-aminoindan compounds, a process for their preparation and pharmaceutical compositions containing them - Google Patents
New 2-aminoindan compounds, a process for their preparation and pharmaceutical compositions containing them Download PDFInfo
- Publication number
- AU725756B2 AU725756B2 AU56359/98A AU5635998A AU725756B2 AU 725756 B2 AU725756 B2 AU 725756B2 AU 56359/98 A AU56359/98 A AU 56359/98A AU 5635998 A AU5635998 A AU 5635998A AU 725756 B2 AU725756 B2 AU 725756B2
- Authority
- AU
- Australia
- Prior art keywords
- dihydro
- benzodioxin
- piperidine
- fumarate
- compound
- 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.)
- Ceased
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- 238000000034 method Methods 0.000 title claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 230000008569 process Effects 0.000 title claims description 5
- LMHHFZAXSANGGM-UHFFFAOYSA-N 2-aminoindane Chemical class C1=CC=C2CC(N)CC2=C1 LMHHFZAXSANGGM-UHFFFAOYSA-N 0.000 title abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 230000003287 optical effect Effects 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 72
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 50
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 34
- -1 (indan-2-yl)amino- -1 -(thiochroman- 8-yl)piperidine Chemical compound 0.000 claims description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
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- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 6
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- 239000007858 starting material Substances 0.000 claims description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
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- 125000001424 substituent group Chemical group 0.000 claims description 4
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- 150000007513 acids Chemical class 0.000 claims description 2
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- 125000004130 indan-2-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])(*)C2([H])[H] 0.000 claims description 2
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- 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 description 2
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- FKSPATRLBQPGIQ-UHFFFAOYSA-N 2-[[1-(2,3-dihydro-1,4-benzodioxin-5-yl)piperidin-4-yl]amino]-2,3-dihydro-1h-inden-5-ol Chemical compound O1CCOC2=C1C=CC=C2N(CC1)CCC1NC1CC2=CC=C(O)C=C2C1 FKSPATRLBQPGIQ-UHFFFAOYSA-N 0.000 claims 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 2
- IMVGGCKYFHDIGP-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-5-yl)-n-(5-nitro-2,3-dihydro-1h-inden-2-yl)piperidin-4-amine Chemical compound O1CCOC2=C1C=CC=C2N(CC1)CCC1NC1CC2=CC=C([N+](=O)[O-])C=C2C1 IMVGGCKYFHDIGP-UHFFFAOYSA-N 0.000 claims 1
- VPVYSMHKTMCEEJ-UHFFFAOYSA-N 1-(3,4-dihydro-2h-chromen-8-yl)-n-[5-(1,2,4-triazol-4-yl)-2,3-dihydro-1h-inden-2-yl]piperidin-4-amine Chemical compound C=1C=C2CC(NC3CCN(CC3)C=3C=4OCCCC=4C=CC=3)CC2=CC=1N1C=NN=C1 VPVYSMHKTMCEEJ-UHFFFAOYSA-N 0.000 claims 1
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- UODHQPDDZXEWTB-WXXKFALUSA-N O1CCCC2=CC=CC(=C12)N1CCC(CC1)NC1CC2=CC=C(C=C2C1)OC.C(\C=C\C(=O)O)(=O)O.O1CCCC2=CC=CC(=C12)N1CCC(CC1)NC1CC2=CC=C(C=C2C1)OC Chemical compound O1CCCC2=CC=CC(=C12)N1CCC(CC1)NC1CC2=CC=C(C=C2C1)OC.C(\C=C\C(=O)O)(=O)O.O1CCCC2=CC=CC(=C12)N1CCC(CC1)NC1CC2=CC=C(C=C2C1)OC UODHQPDDZXEWTB-WXXKFALUSA-N 0.000 claims 1
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- MIJBHSBEKPGHDQ-UHFFFAOYSA-N n-(3h-cyclopenta[f][2,1,3]benzoxadiazol-6-yl)acetamide Chemical compound C=1C2=NONC2=CC2=CC(NC(=O)C)=CC2=1 MIJBHSBEKPGHDQ-UHFFFAOYSA-N 0.000 description 1
- HMTMYYKVAGYEEW-UHFFFAOYSA-N n-(5-amino-6-nitro-2,3-dihydro-1h-inden-2-yl)acetamide Chemical compound NC1=C([N+]([O-])=O)C=C2CC(NC(=O)C)CC2=C1 HMTMYYKVAGYEEW-UHFFFAOYSA-N 0.000 description 1
- COGGGWRHZQTITF-UHFFFAOYSA-N n-(oxan-4-ylidene)hydroxylamine Chemical compound ON=C1CCOCC1 COGGGWRHZQTITF-UHFFFAOYSA-N 0.000 description 1
- DLBUCYGKKXLHOG-UHFFFAOYSA-N n-[1-(2,3-dihydro-1,4-benzodioxin-5-yl)-4-methylpiperidin-4-yl]acetamide Chemical compound C1CC(NC(=O)C)(C)CCN1C1=CC=CC2=C1OCCO2 DLBUCYGKKXLHOG-UHFFFAOYSA-N 0.000 description 1
- OCRMQBFUELEDCA-UHFFFAOYSA-N n-[1-(3,4-dihydro-2h-chromen-8-yl)piperidin-4-ylidene]hydroxylamine Chemical compound C1CC(=NO)CCN1C1=CC=CC2=C1OCCC2 OCRMQBFUELEDCA-UHFFFAOYSA-N 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 210000001640 nerve ending Anatomy 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 230000001272 neurogenic effect Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- KWZSCXIYGVEHOB-UHFFFAOYSA-N oxan-4-amine;hydrochloride Chemical compound [Cl-].[NH3+]C1CCOCC1 KWZSCXIYGVEHOB-UHFFFAOYSA-N 0.000 description 1
- JMJRYTGVHCAYCT-UHFFFAOYSA-N oxan-4-one Chemical compound O=C1CCOCC1 JMJRYTGVHCAYCT-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical compound C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 description 1
- 230000001242 postsynaptic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000020341 sensory perception of pain Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- AIMUHNZKNFEZSN-UHFFFAOYSA-M sodium;decane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCS([O-])(=O)=O AIMUHNZKNFEZSN-UHFFFAOYSA-M 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- ZZIZZTHXZRDOFM-XFULWGLBSA-N tamsulosin hydrochloride Chemical compound [H+].[Cl-].CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1 ZZIZZTHXZRDOFM-XFULWGLBSA-N 0.000 description 1
- WDXFFIGEJMZUMO-UHFFFAOYSA-N tert-butyl n-(2,3-dihydro-1,4-benzoxathiin-5-yl)carbamate Chemical compound O1CCSC2=C1C=CC=C2NC(=O)OC(C)(C)C WDXFFIGEJMZUMO-UHFFFAOYSA-N 0.000 description 1
- ZCDQUMICDAFZJZ-UHFFFAOYSA-N tert-butyl n-(3,4-dihydro-2h-thiochromen-8-yl)carbamate Chemical compound C1CCSC2=C1C=CC=C2NC(=O)OC(C)(C)C ZCDQUMICDAFZJZ-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 230000026683 transduction Effects 0.000 description 1
- 238000010361 transduction Methods 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P25/18—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
- A61P25/24—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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Anesthesiology (AREA)
- Child & Adolescent Psychology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR97/02360 | 1997-02-27 | ||
| FR9702360A FR2760014B1 (fr) | 1997-02-27 | 1997-02-27 | Nouveaux composes de 2-amino indane, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU5635998A AU5635998A (en) | 1998-09-03 |
| AU725756B2 true AU725756B2 (en) | 2000-10-19 |
Family
ID=9504253
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU56359/98A Ceased AU725756B2 (en) | 1997-02-27 | 1998-02-27 | New 2-aminoindan compounds, a process for their preparation and pharmaceutical compositions containing them |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5968954A (enExample) |
| EP (1) | EP0861837B1 (enExample) |
| JP (1) | JPH10237071A (enExample) |
| CN (1) | CN1090627C (enExample) |
| AT (1) | ATE265451T1 (enExample) |
| AU (1) | AU725756B2 (enExample) |
| BR (1) | BR9800763A (enExample) |
| CA (1) | CA2231025C (enExample) |
| DE (1) | DE69823411T2 (enExample) |
| DK (1) | DK0861837T3 (enExample) |
| ES (1) | ES2219853T3 (enExample) |
| FR (1) | FR2760014B1 (enExample) |
| HU (1) | HU224312B1 (enExample) |
| NO (1) | NO314307B1 (enExample) |
| NZ (1) | NZ329853A (enExample) |
| PL (1) | PL190240B1 (enExample) |
| PT (1) | PT861837E (enExample) |
| ZA (1) | ZA981680B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI274750B (en) * | 1999-01-12 | 2007-03-01 | Abbott Gmbh & Co Kg | Triazole compounds showing high affinity to dopamine D3 receptor and pharmaceutical composition comprising the same |
| SE0103650D0 (sv) * | 2001-11-01 | 2001-11-01 | Astrazeneca Ab | Therapeutic heterocyclic compounds |
| KR100864356B1 (ko) * | 2001-01-16 | 2008-10-17 | 아스트라제네카 아베 | 치료용 헤테로시클릭 화합물 |
| DE60231507D1 (de) | 2001-07-20 | 2010-07-01 | Psychogenics Inc | Behandlung von hyperaktivitätsstörungen und aufmerksamkeitsdefiziten |
| JP2005343790A (ja) * | 2002-05-31 | 2005-12-15 | Ajinomoto Co Inc | カルシウムチャネル拮抗薬を含有する医薬組成物 |
| US20050165025A1 (en) * | 2004-01-22 | 2005-07-28 | Recordati Ireland Ltd. | Combination therapy with 5HT 1A and 5HT 1B-receptor antagonists |
| WO2006062063A1 (ja) * | 2004-12-08 | 2006-06-15 | Astellas Pharma Inc. | ピペリジン誘導体及びその製造法 |
| UY29892A1 (es) * | 2005-11-04 | 2007-06-29 | Astrazeneca Ab | Nuevos derivados de cromano, composiciones farmaceuticas conteniendolos, procesos de preparacion y aplicaciones |
| WO2020183011A1 (en) | 2019-03-14 | 2020-09-17 | Institut Curie | Htr1d inhibitors and uses thereof in the treatment of cancer |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9318431D0 (en) * | 1993-09-06 | 1993-10-20 | Boots Co Plc | Therapeutic agents |
| FR2734819B1 (fr) * | 1995-05-31 | 1997-07-04 | Adir | Nouveaux composes de la piperazine, de la piperidine et de la 1,2,5,6-tetrahydropyridine, leur procede de preparation et les compositions pharmaceutiques les contenant |
-
1997
- 1997-02-27 FR FR9702360A patent/FR2760014B1/fr not_active Expired - Fee Related
-
1998
- 1998-02-24 PL PL98324982A patent/PL190240B1/pl not_active IP Right Cessation
- 1998-02-25 JP JP10042716A patent/JPH10237071A/ja active Pending
- 1998-02-25 BR BR9800763-7A patent/BR9800763A/pt not_active Application Discontinuation
- 1998-02-26 CA CA002231025A patent/CA2231025C/fr not_active Expired - Fee Related
- 1998-02-26 HU HU9800422A patent/HU224312B1/hu not_active IP Right Cessation
- 1998-02-26 NO NO19980803A patent/NO314307B1/no unknown
- 1998-02-26 US US09/031,490 patent/US5968954A/en not_active Expired - Fee Related
- 1998-02-26 CN CN98107709A patent/CN1090627C/zh not_active Expired - Fee Related
- 1998-02-26 NZ NZ329853A patent/NZ329853A/xx unknown
- 1998-02-27 DE DE69823411T patent/DE69823411T2/de not_active Expired - Fee Related
- 1998-02-27 AU AU56359/98A patent/AU725756B2/en not_active Ceased
- 1998-02-27 ES ES98400469T patent/ES2219853T3/es not_active Expired - Lifetime
- 1998-02-27 ZA ZA981680A patent/ZA981680B/xx unknown
- 1998-02-27 PT PT98400469T patent/PT861837E/pt unknown
- 1998-02-27 AT AT98400469T patent/ATE265451T1/de not_active IP Right Cessation
- 1998-02-27 EP EP98400469A patent/EP0861837B1/fr not_active Expired - Lifetime
- 1998-02-27 DK DK98400469T patent/DK0861837T3/da active
Also Published As
| Publication number | Publication date |
|---|---|
| CN1194983A (zh) | 1998-10-07 |
| DE69823411T2 (de) | 2005-02-17 |
| NZ329853A (en) | 1999-01-28 |
| JPH10237071A (ja) | 1998-09-08 |
| DE69823411D1 (de) | 2004-06-03 |
| EP0861837B1 (fr) | 2004-04-28 |
| FR2760014B1 (fr) | 1999-04-09 |
| PT861837E (pt) | 2004-07-30 |
| HU224312B1 (hu) | 2005-07-28 |
| ES2219853T3 (es) | 2004-12-01 |
| HK1014945A1 (en) | 1999-10-08 |
| HUP9800422A1 (hu) | 1999-12-28 |
| PL324982A1 (en) | 1998-08-31 |
| CA2231025C (fr) | 2003-09-16 |
| HU9800422D0 (en) | 1998-04-28 |
| ZA981680B (en) | 1998-09-04 |
| AU5635998A (en) | 1998-09-03 |
| NO980803L (no) | 1998-08-28 |
| DK0861837T3 (da) | 2004-08-16 |
| BR9800763A (pt) | 1999-12-07 |
| CA2231025A1 (fr) | 1998-08-27 |
| PL190240B1 (pl) | 2005-11-30 |
| FR2760014A1 (fr) | 1998-08-28 |
| EP0861837A1 (fr) | 1998-09-02 |
| CN1090627C (zh) | 2002-09-11 |
| ATE265451T1 (de) | 2004-05-15 |
| NO314307B1 (no) | 2003-03-03 |
| US5968954A (en) | 1999-10-19 |
| NO980803D0 (no) | 1998-02-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| PC | Assignment registered |
Owner name: LES LABORATOIRES SERVIER Free format text: FORMER OWNER WAS: ADIR ET COMPAGNIE |