ZA200403095B - Derivatives of 4-(thio-or selenoxanthene-9-ylidene)-piperidine or acridine and its use as a selective 5-HT2B receptor antagonist. - Google Patents
Derivatives of 4-(thio-or selenoxanthene-9-ylidene)-piperidine or acridine and its use as a selective 5-HT2B receptor antagonist. Download PDFInfo
- Publication number
- ZA200403095B ZA200403095B ZA200403095A ZA200403095A ZA200403095B ZA 200403095 B ZA200403095 B ZA 200403095B ZA 200403095 A ZA200403095 A ZA 200403095A ZA 200403095 A ZA200403095 A ZA 200403095A ZA 200403095 B ZA200403095 B ZA 200403095B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- piperidine
- ethoxy
- yliden
- thioxanthen
- Prior art date
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- -1 selenoxanthene-9-ylidene Chemical group 0.000 title claims abstract description 31
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 title abstract description 8
- 229940044551 receptor antagonist Drugs 0.000 title description 31
- 239000002464 receptor antagonist Substances 0.000 title description 31
- 102000006969 5-HT2B Serotonin Receptor Human genes 0.000 title 1
- 108010072584 5-HT2B Serotonin Receptor Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 44
- 201000010099 disease Diseases 0.000 claims abstract description 33
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 239000003814 drug Substances 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 48
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 17
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
- 208000002193 Pain Diseases 0.000 claims description 14
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 11
- 206010020772 Hypertension Diseases 0.000 claims description 11
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 11
- 208000035475 disorder Diseases 0.000 claims description 11
- 208000006673 asthma Diseases 0.000 claims description 10
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 10
- 208000019695 Migraine disease Diseases 0.000 claims description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 9
- 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 claims description 9
- 206010027599 migraine Diseases 0.000 claims description 9
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 9
- 208000037803 restenosis Diseases 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 230000036407 pain Effects 0.000 claims description 8
- 239000005557 antagonist Substances 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 208000023504 respiratory system disease Diseases 0.000 claims description 7
- OFQLDZMPIOGDNJ-UHFFFAOYSA-N 3-ethoxy-9-(1-methylpiperidin-4-ylidene)-10h-acridine Chemical compound C12=CC=CC=C2NC2=CC(OCC)=CC=C2C1=C1CCN(C)CC1 OFQLDZMPIOGDNJ-UHFFFAOYSA-N 0.000 claims description 6
- FEWUSHKVJYSQIB-UHFFFAOYSA-N 4-(6-ethoxy-1-ethylthioxanthen-9-ylidene)-1-methylpiperidine Chemical compound C12=C(CC)C=CC=C2SC2=CC(OCC)=CC=C2C1=C1CCN(C)CC1 FEWUSHKVJYSQIB-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 230000004899 motility Effects 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 229910052711 selenium Inorganic materials 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- XWOIDMWRCUFUQE-UHFFFAOYSA-N 4-(1-methoxy-6-propan-2-ylthioxanthen-9-ylidene)-1-methylpiperidine Chemical compound C1=2C(OC)=CC=CC=2SC2=CC(C(C)C)=CC=C2C1=C1CCN(C)CC1 XWOIDMWRCUFUQE-UHFFFAOYSA-N 0.000 claims description 5
- IVUNAHCWRQJVCN-UHFFFAOYSA-N 4-(3-ethoxy-5-ethylthioxanthen-9-ylidene)-1-methylpiperidine Chemical compound C12=CC=CC(CC)=C2SC2=CC(OCC)=CC=C2C1=C1CCN(C)CC1 IVUNAHCWRQJVCN-UHFFFAOYSA-N 0.000 claims description 5
- OEDPXWIEAHTGJG-UHFFFAOYSA-N 4-(3-ethoxyselenoxanthen-9-ylidene)-1-methylpiperidine Chemical compound C12=CC=CC=C2[Se]C2=CC(OCC)=CC=C2C1=C1CCN(C)CC1 OEDPXWIEAHTGJG-UHFFFAOYSA-N 0.000 claims description 5
- ZFHHRACTJNGKKP-UHFFFAOYSA-N 6-ethoxy-1-methoxy-9-(1-methylpiperidin-4-ylidene)-10h-acridine Chemical compound C1=CC=C(OC)C2=C1NC1=CC(OCC)=CC=C1C2=C1CCN(C)CC1 ZFHHRACTJNGKKP-UHFFFAOYSA-N 0.000 claims description 5
- YMTDTSKJKGAAPG-UHFFFAOYSA-N 8-methoxy-n,n-dimethyl-9-(1-methylpiperidin-4-ylidene)thioxanthen-3-amine Chemical compound C1=2C(OC)=CC=CC=2SC2=CC(N(C)C)=CC=C2C1=C1CCN(C)CC1 YMTDTSKJKGAAPG-UHFFFAOYSA-N 0.000 claims description 5
- 206010065390 Inflammatory pain Diseases 0.000 claims description 5
- 230000000414 obstructive effect Effects 0.000 claims description 5
- 201000011264 priapism Diseases 0.000 claims description 5
- MBQKFAYULMPBSZ-UHFFFAOYSA-N 3-ethoxy-9-(1-methylpiperidin-4-ylidene)selenoxanthen-1-ol Chemical compound C12=CC=CC=C2[Se]C2=CC(OCC)=CC(O)=C2C1=C1CCN(C)CC1 MBQKFAYULMPBSZ-UHFFFAOYSA-N 0.000 claims description 4
- FAKWDZQLFFHYKZ-UHFFFAOYSA-N 4-(3-ethoxy-1-methoxyselenoxanthen-9-ylidene)-1-methylpiperidine Chemical compound C12=CC=CC=C2[Se]C2=CC(OCC)=CC(OC)=C2C1=C1CCN(C)CC1 FAKWDZQLFFHYKZ-UHFFFAOYSA-N 0.000 claims description 4
- KKTNSZUKKLGNND-UHFFFAOYSA-N 4-(3-ethoxy-4-ethylthioxanthen-9-ylidene)-1-methylpiperidine Chemical compound C12=CC=CC=C2SC2=C(CC)C(OCC)=CC=C2C1=C1CCN(C)CC1 KKTNSZUKKLGNND-UHFFFAOYSA-N 0.000 claims description 4
- ZBMRDYORLQSJFW-UHFFFAOYSA-N 4-(3-ethoxy-4-methylthioxanthen-9-ylidene)-1-methylpiperidine Chemical compound C12=CC=CC=C2SC2=C(C)C(OCC)=CC=C2C1=C1CCN(C)CC1 ZBMRDYORLQSJFW-UHFFFAOYSA-N 0.000 claims description 4
- ANZVBVKYXOGOQC-UHFFFAOYSA-N 4-(6-ethoxy-1-methoxythioxanthen-9-ylidene)-1-methylpiperidine Chemical compound C12=C(OC)C=CC=C2SC2=CC(OCC)=CC=C2C1=C1CCN(C)CC1 ANZVBVKYXOGOQC-UHFFFAOYSA-N 0.000 claims description 4
- LPLKBXNDRGRNFU-UHFFFAOYSA-N 6-(dimethylamino)-9-(1-methylpiperidin-4-ylidene)thioxanthen-1-ol Chemical compound C12=C(O)C=CC=C2SC2=CC(N(C)C)=CC=C2C1=C1CCN(C)CC1 LPLKBXNDRGRNFU-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 206010058019 Cancer Pain Diseases 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 208000004296 neuralgia Diseases 0.000 claims description 4
- 208000021722 neuropathic pain Diseases 0.000 claims description 4
- JQCOAJQGICQZPJ-UHFFFAOYSA-N 2-N-ethyl-2-N-fluoro-1-N',1-N'-dimethylethane-1,1,2-triamine Chemical compound CCN(F)CC(N)N(C)C JQCOAJQGICQZPJ-UHFFFAOYSA-N 0.000 claims description 3
- YHONHMAGTJGBIT-UHFFFAOYSA-N 4-(3-ethoxythioxanthen-9-ylidene)-1,3-dimethylpiperidine Chemical compound C12=CC=CC=C2SC2=CC(OCC)=CC=C2C1=C1CCN(C)CC1C YHONHMAGTJGBIT-UHFFFAOYSA-N 0.000 claims description 3
- PTFLPVREBRGPNM-UHFFFAOYSA-N 6-ethoxy-9-(1-methylpiperidin-4-ylidene)-10h-acridin-1-ol Chemical compound C12=C(O)C=CC=C2NC2=CC(OCC)=CC=C2C1=C1CCN(C)CC1 PTFLPVREBRGPNM-UHFFFAOYSA-N 0.000 claims description 3
- DPWCIMKXIGJGIU-UHFFFAOYSA-N 6-ethoxy-9-(1-methylpiperidin-4-ylidene)thioxanthen-1-ol Chemical compound C12=C(O)C=CC=C2SC2=CC(OCC)=CC=C2C1=C1CCN(C)CC1 DPWCIMKXIGJGIU-UHFFFAOYSA-N 0.000 claims description 3
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- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 3
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- ATLBDAYYADTLFI-UHFFFAOYSA-N 4-(1,6-dimethoxythioxanthen-9-ylidene)-1-methylpiperidine Chemical compound C12=C(OC)C=CC=C2SC2=CC(OC)=CC=C2C1=C1CCN(C)CC1 ATLBDAYYADTLFI-UHFFFAOYSA-N 0.000 claims description 2
- 238000003747 Grignard reaction Methods 0.000 claims description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims 5
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- VGKLJIARACVWDQ-UHFFFAOYSA-N N-[amino(trifluoromethoxy)-lambda3-bromanyl]-N-methylmethanamine Chemical compound FC(OBr(N(C)C)N)(F)F VGKLJIARACVWDQ-UHFFFAOYSA-N 0.000 claims 1
- 229940116892 5 Hydroxytryptamine 2B receptor antagonist Drugs 0.000 abstract 1
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- 238000003786 synthesis reaction Methods 0.000 description 17
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- 230000001225 therapeutic effect Effects 0.000 description 14
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- 231100000252 nontoxic Toxicity 0.000 description 7
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- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 6
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
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- 150000003053 piperidines Chemical class 0.000 description 6
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- SFCRDCSJCHFDTQ-UHFFFAOYSA-N 4-thioxanthen-9-ylidenepiperidine Chemical compound C1CNCCC1=C1C2=CC=CC=C2SC2=CC=CC=C21 SFCRDCSJCHFDTQ-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- 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
- A61P9/12—Antihypertensives
-
- 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
- C07D421/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D421/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing two hetero rings
- C07D421/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as 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)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01125527A EP1306376A1 (fr) | 2001-10-25 | 2001-10-25 | Dérives de 4-(thio- or selenoxanthene-9-ylidene)-piperidine ou acridine et leur application comme antagonistes selectives de 5-HT2B |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200403095B true ZA200403095B (en) | 2005-01-25 |
Family
ID=8179078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200403095A ZA200403095B (en) | 2001-10-25 | 2004-04-22 | Derivatives of 4-(thio-or selenoxanthene-9-ylidene)-piperidine or acridine and its use as a selective 5-HT2B receptor antagonist. |
Country Status (14)
| Country | Link |
|---|---|
| EP (2) | EP1306376A1 (fr) |
| JP (1) | JP4452501B2 (fr) |
| KR (1) | KR100921214B1 (fr) |
| CN (1) | CN100345843C (fr) |
| AT (1) | ATE301119T1 (fr) |
| AU (1) | AU2002350603B2 (fr) |
| CA (1) | CA2462416C (fr) |
| DE (1) | DE60205397T2 (fr) |
| DK (1) | DK1438307T3 (fr) |
| ES (1) | ES2246416T3 (fr) |
| HK (1) | HK1073311A1 (fr) |
| RU (1) | RU2314305C2 (fr) |
| WO (1) | WO2003035646A2 (fr) |
| ZA (1) | ZA200403095B (fr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004057338A1 (fr) * | 2002-12-23 | 2004-07-08 | Bayer Healthcare Ag | Diagnostic et traitement de maladies associees au recepteur 2b (5-hteb) de 5-hydroxytryptamine (serotonine) |
| BRPI0411998A (pt) * | 2003-06-27 | 2006-09-05 | Janssen Pharmaceutica Nv | moduladores delta-opióides tricìclicos |
| WO2007030089A1 (fr) | 2004-08-05 | 2007-03-15 | Janssen Pharmaceutica N.V. | Modulateurs d’opioïdes delta tricycliques |
| US7439239B2 (en) | 2004-12-22 | 2008-10-21 | Janssen Pharmaceutica N.V. | Tricyclic δ- opioid modulators |
| BRPI0519201A2 (pt) | 2004-12-22 | 2008-12-30 | Janssen Pharmaceutica Nv | moduladores de delta-opiàide tricÍclico |
| CN101128460A (zh) | 2005-01-06 | 2008-02-20 | 詹森药业有限公司 | 三环的δ-阿片样物质调节剂 |
| WO2006138528A2 (fr) | 2005-06-16 | 2006-12-28 | Janssen Pharmaceutica N.V | Modulateurs d'opioides tricycliques |
| WO2008124184A1 (fr) * | 2007-04-09 | 2008-10-16 | Xvasive Inc. | Traitement de céphalées, de cervicalgie, d'arthralgie et de douleur de type inflammatoire |
| WO2014117863A1 (fr) | 2013-02-01 | 2014-08-07 | Biofrontera Bioscience Gmbh | Formes polymorphes de sels d'addition d'acide de thioxanthène-9-ylidène-1-méthylpipéridines utilisés comme composés antimigraineux |
| KR102105682B1 (ko) | 2018-08-29 | 2020-04-28 | 성균관대학교산학협력단 | 신규 2-아실 아크리딘 유도체, 이의 제조방법, 및 이를 유효성분으로 포함하는 암 예방 또는 치료용 조성물 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL122808C (fr) * | 1961-09-29 | |||
| NL301204A (fr) * | 1962-12-07 | |||
| NL6818027A (fr) * | 1968-01-09 | 1969-07-11 | ||
| BE791699A (fr) * | 1971-11-22 | 1973-05-21 | Sandoz Sa | Nouveaux derives du thioxanthene, leur preparation et leur application comme medicaments |
| US4086350A (en) * | 1974-11-06 | 1978-04-25 | Smithkline Corporation | Pharmaceutical compositions and method of producing anti-psychotic activity without extrapyramidal symptoms |
| ZA756550B (en) * | 1974-11-06 | 1976-09-29 | Smithkline Corp | Pharmaceutical compositions and method of producing antipsychotic activity without extrapyramidal symptoms |
| US4285956A (en) * | 1978-05-12 | 1981-08-25 | Kefalas A/S | Xanthene and thioxanthene derivatives, compositions thereof and treatment therewith |
| US4777177A (en) * | 1984-10-19 | 1988-10-11 | Ciba-Geigy Corporation | Pesticidal thioxanthen-9-ylidenepiperidines |
-
2001
- 2001-10-25 EP EP01125527A patent/EP1306376A1/fr not_active Withdrawn
-
2002
- 2002-10-23 AU AU2002350603A patent/AU2002350603B2/en not_active Ceased
- 2002-10-23 JP JP2003538162A patent/JP4452501B2/ja not_active Expired - Fee Related
- 2002-10-23 KR KR1020047006240A patent/KR100921214B1/ko not_active IP Right Cessation
- 2002-10-23 RU RU2004116070/04A patent/RU2314305C2/ru not_active IP Right Cessation
- 2002-10-23 EP EP02785280A patent/EP1438307B1/fr not_active Expired - Lifetime
- 2002-10-23 DK DK02785280T patent/DK1438307T3/da active
- 2002-10-23 DE DE60205397T patent/DE60205397T2/de not_active Expired - Lifetime
- 2002-10-23 AT AT02785280T patent/ATE301119T1/de active
- 2002-10-23 CN CNB028210700A patent/CN100345843C/zh not_active Expired - Fee Related
- 2002-10-23 ES ES02785280T patent/ES2246416T3/es not_active Expired - Lifetime
- 2002-10-23 CA CA2462416A patent/CA2462416C/fr not_active Expired - Fee Related
- 2002-10-23 WO PCT/EP2002/011817 patent/WO2003035646A2/fr active IP Right Grant
-
2004
- 2004-04-22 ZA ZA200403095A patent/ZA200403095B/en unknown
-
2005
- 2005-07-19 HK HK05106095A patent/HK1073311A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| RU2004116070A (ru) | 2005-11-10 |
| WO2003035646A2 (fr) | 2003-05-01 |
| CA2462416C (fr) | 2011-04-26 |
| ATE301119T1 (de) | 2005-08-15 |
| DK1438307T3 (da) | 2005-12-12 |
| JP2005510504A (ja) | 2005-04-21 |
| CA2462416A1 (fr) | 2003-05-01 |
| EP1306376A1 (fr) | 2003-05-02 |
| KR100921214B1 (ko) | 2009-10-09 |
| DE60205397T2 (de) | 2006-05-24 |
| AU2002350603B2 (en) | 2008-02-28 |
| CN100345843C (zh) | 2007-10-31 |
| RU2314305C2 (ru) | 2008-01-10 |
| WO2003035646A3 (fr) | 2003-09-04 |
| HK1073311A1 (en) | 2005-09-30 |
| JP4452501B2 (ja) | 2010-04-21 |
| CN1575291A (zh) | 2005-02-02 |
| KR20040047982A (ko) | 2004-06-05 |
| DE60205397D1 (de) | 2005-09-08 |
| EP1438307B1 (fr) | 2005-08-03 |
| EP1438307A2 (fr) | 2004-07-21 |
| ES2246416T3 (es) | 2006-02-16 |
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