PL208647B1 - Tetrahydropirydylo-alkilo-benzodiazyny, sposób ich wytwarzania, środek farmaceutyczny, zastosowanie, lek oraz związki pośrednie - Google Patents
Tetrahydropirydylo-alkilo-benzodiazyny, sposób ich wytwarzania, środek farmaceutyczny, zastosowanie, lek oraz związki pośrednieInfo
- Publication number
- PL208647B1 PL208647B1 PL370832A PL37083202A PL208647B1 PL 208647 B1 PL208647 B1 PL 208647B1 PL 370832 A PL370832 A PL 370832A PL 37083202 A PL37083202 A PL 37083202A PL 208647 B1 PL208647 B1 PL 208647B1
- Authority
- PL
- Poland
- Prior art keywords
- phenyl
- ethyl
- tetrahydropyridine
- pyridyl
- trifluoromethylphenyl
- Prior art date
Links
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims description 8
- 230000000694 effects Effects 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 95
- 150000003839 salts Chemical class 0.000 claims abstract description 33
- 239000012453 solvate Substances 0.000 claims abstract description 25
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 40
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 239000004480 active ingredient Substances 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 206010061218 Inflammation Diseases 0.000 claims description 4
- 230000004054 inflammatory process Effects 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- AVLSWKAQOQPIJX-UHFFFAOYSA-N 2-[4-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=CC(=CC=3)C=3N=CC=CC=3)CC=2)=C1 AVLSWKAQOQPIJX-UHFFFAOYSA-N 0.000 claims description 3
- GSZGXVFNJYIXSU-UHFFFAOYSA-N 2-methyl-5-[4-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]pyridine Chemical compound C1=NC(C)=CC=C1C(C=C1)=CC=C1CCN1CC=C(C=2C=C(C=CC=2)C(F)(F)F)CC1 GSZGXVFNJYIXSU-UHFFFAOYSA-N 0.000 claims description 3
- VRVWULKTIUHPGX-UHFFFAOYSA-N 3-[3-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]pyridine Chemical class FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=C(C=CC=3)C=3C=NC=CC=3)CC=2)=C1 VRVWULKTIUHPGX-UHFFFAOYSA-N 0.000 claims description 3
- WQZHBVMNFSQWGI-UHFFFAOYSA-N 3-[4-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=CC(=CC=3)C=3C=NC=CC=3)CC=2)=C1 WQZHBVMNFSQWGI-UHFFFAOYSA-N 0.000 claims description 3
- IXYDBBSEBBTUDK-UHFFFAOYSA-N 4-[3-[2-[1-oxido-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-ium-1-yl]ethyl]phenyl]pyridine Chemical compound C1CC(C=2C=C(C=CC=2)C(F)(F)F)=CC[N+]1([O-])CCC(C=1)=CC=CC=1C1=CC=NC=C1 IXYDBBSEBBTUDK-UHFFFAOYSA-N 0.000 claims description 3
- USRDGDMBBSRPAQ-UHFFFAOYSA-N 4-[3-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=C(C=CC=3)C=3C=CN=CC=3)CC=2)=C1 USRDGDMBBSRPAQ-UHFFFAOYSA-N 0.000 claims description 3
- UZZMVDOPBJYQBP-UHFFFAOYSA-N 4-[4-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=CC(=CC=3)C=3C=CN=CC=3)CC=2)=C1 UZZMVDOPBJYQBP-UHFFFAOYSA-N 0.000 claims description 3
- PCBSZJZMHIUKIR-UHFFFAOYSA-N 5-[4-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]pyrimidine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=CC(=CC=3)C=3C=NC=NC=3)CC=2)=C1 PCBSZJZMHIUKIR-UHFFFAOYSA-N 0.000 claims description 3
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- GGKLVYAFNZGPOP-UHFFFAOYSA-N 2-[3-[2-[4-(3-fluorophenyl)-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]pyridine Chemical compound FC1=CC=CC(C=2CCN(CCC=3C=C(C=CC=3)C=3N=CC=CC=3)CC=2)=C1 GGKLVYAFNZGPOP-UHFFFAOYSA-N 0.000 claims description 2
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- OMTLYGNWDBVLFE-UHFFFAOYSA-N 2-[3-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=C(C=CC=3)C=3N=CC=CC=3)CC=2)=C1 OMTLYGNWDBVLFE-UHFFFAOYSA-N 0.000 claims description 2
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- MVYFZCVMGBTQIE-UHFFFAOYSA-N 2-chloro-6-[1-[2-(3-pyridin-4-ylphenyl)ethyl]-3,6-dihydro-2h-pyridin-4-yl]pyridine Chemical compound ClC1=CC=CC(C=2CCN(CCC=3C=C(C=CC=3)C=3C=CN=CC=3)CC=2)=N1 MVYFZCVMGBTQIE-UHFFFAOYSA-N 0.000 claims description 2
- UFZYFKMZPPOFND-UHFFFAOYSA-N 2-methyl-5-[3-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]pyridine Chemical compound C1=NC(C)=CC=C1C1=CC=CC(CCN2CC=C(CC2)C=2C=C(C=CC=2)C(F)(F)F)=C1 UFZYFKMZPPOFND-UHFFFAOYSA-N 0.000 claims description 2
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- 229940050411 fumarate Drugs 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
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- 239000003112 inhibitor Substances 0.000 description 1
- 208000036971 interstitial lung disease 2 Diseases 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 229960004584 methylprednisolone Drugs 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000005012 myelin Anatomy 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
- 239000008203 oral pharmaceutical composition Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229940125422 potassium channel blocker Drugs 0.000 description 1
- 239000003450 potassium channel blocker Substances 0.000 description 1
- 229960004618 prednisone Drugs 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
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- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 208000005069 pulmonary fibrosis Diseases 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 210000005222 synovial tissue Anatomy 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- C07D401/10—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 linked by a carbon chain containing aromatic rings
-
- 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
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- A61P11/06—Antiasthmatics
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A—HUMAN NECESSITIES
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- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
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- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Ophthalmology & Optometry (AREA)
- Virology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Dermatology (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0114897A FR2832405B1 (fr) | 2001-11-19 | 2001-11-19 | Tetrahydropyridyl-alkyl-heterocycles azotes, procede pour leur preparation et compositions pharmaceutiques les contenant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL370832A1 PL370832A1 (en) | 2005-05-30 |
| PL208647B1 true PL208647B1 (pl) | 2011-05-31 |
Family
ID=8869506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL370832A PL208647B1 (pl) | 2001-11-19 | 2002-11-18 | Tetrahydropirydylo-alkilo-benzodiazyny, sposób ich wytwarzania, środek farmaceutyczny, zastosowanie, lek oraz związki pośrednie |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7211578B2 (https=) |
| EP (1) | EP1448550B1 (https=) |
| JP (1) | JP4603794B2 (https=) |
| AT (1) | ATE499359T1 (https=) |
| AU (1) | AU2002356244B2 (https=) |
| CA (1) | CA2464721C (https=) |
| DE (1) | DE60239284D1 (https=) |
| FR (1) | FR2832405B1 (https=) |
| HU (1) | HUP0402229A3 (https=) |
| MX (1) | MXPA04004760A (https=) |
| PL (1) | PL208647B1 (https=) |
| WO (1) | WO2003044010A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200840566A (en) * | 2006-12-22 | 2008-10-16 | Esteve Labor Dr | Heterocyclyl-substituted-ethylamino-phenyl derivatives, their preparation and use as medicaments |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4885572A (https=) * | 1972-02-17 | 1973-11-13 | ||
| JPS49100090A (https=) * | 1973-01-30 | 1974-09-20 | ||
| JPS49100089A (https=) * | 1973-01-30 | 1974-09-20 | ||
| JPS5236B2 (https=) * | 1973-03-28 | 1977-01-05 | ||
| JPS5046669A (https=) * | 1973-03-28 | 1975-04-25 | ||
| DE19517851A1 (de) * | 1995-05-16 | 1996-11-21 | Hoechst Ag | Organometallverbindung |
| FR2757160B1 (fr) | 1996-12-13 | 1999-03-12 | Sanofi Sa | 1-phenylalkyl-1,2,3,6-tetrahydropyridines |
| US6316466B1 (en) * | 1998-05-05 | 2001-11-13 | Syntex (U.S.A.) Llc | Pyrazole derivatives P-38 MAP kinase inhibitors |
| DZ2796A1 (fr) * | 1998-05-21 | 2003-12-01 | Smithkline Beecham Corp | Composés à fonction bis-aminométhyl-carbonyle nouveaux, procédé pour leur préparation et compositions pharmaceutiques les contenant. |
| HK1046532B (zh) * | 1999-10-22 | 2005-03-18 | Sanofi-Aventis | 具有抑制tnf活性的苯基-和吡啶基-四氫吡啶 |
| FR2803593B1 (fr) * | 2000-01-06 | 2002-02-15 | Sanofi Synthelabo | Nouvelles tetrahydropyridines, procede pour leur preparation et compositions pharmaceutiques les contenant |
| SI1283839T1 (https=) * | 2000-05-26 | 2005-08-31 | Schering Corp |
-
2001
- 2001-11-19 FR FR0114897A patent/FR2832405B1/fr not_active Expired - Fee Related
-
2002
- 2002-11-18 JP JP2003545647A patent/JP4603794B2/ja not_active Expired - Fee Related
- 2002-11-18 US US10/495,890 patent/US7211578B2/en not_active Expired - Fee Related
- 2002-11-18 MX MXPA04004760A patent/MXPA04004760A/es active IP Right Grant
- 2002-11-18 CA CA2464721A patent/CA2464721C/en not_active Expired - Fee Related
- 2002-11-18 EP EP02803433A patent/EP1448550B1/fr not_active Expired - Lifetime
- 2002-11-18 DE DE60239284T patent/DE60239284D1/de not_active Expired - Lifetime
- 2002-11-18 PL PL370832A patent/PL208647B1/pl not_active IP Right Cessation
- 2002-11-18 AU AU2002356244A patent/AU2002356244B2/en not_active Ceased
- 2002-11-18 WO PCT/FR2002/003929 patent/WO2003044010A1/fr not_active Ceased
- 2002-11-18 AT AT02803433T patent/ATE499359T1/de not_active IP Right Cessation
- 2002-11-18 HU HU0402229A patent/HUP0402229A3/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003044010A1 (fr) | 2003-05-30 |
| FR2832405B1 (fr) | 2004-12-10 |
| US20050004132A1 (en) | 2005-01-06 |
| PL370832A1 (en) | 2005-05-30 |
| DE60239284D1 (de) | 2011-04-07 |
| JP4603794B2 (ja) | 2010-12-22 |
| EP1448550A1 (fr) | 2004-08-25 |
| JP2005509678A (ja) | 2005-04-14 |
| CA2464721C (en) | 2011-03-08 |
| AU2002356244A1 (en) | 2003-06-10 |
| FR2832405A1 (fr) | 2003-05-23 |
| ATE499359T1 (de) | 2011-03-15 |
| HUP0402229A2 (hu) | 2005-02-28 |
| EP1448550B1 (fr) | 2011-02-23 |
| HUP0402229A3 (en) | 2009-07-28 |
| AU2002356244B2 (en) | 2008-07-24 |
| US7211578B2 (en) | 2007-05-01 |
| MXPA04004760A (es) | 2004-07-30 |
| CA2464721A1 (en) | 2003-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Decisions on the lapse of the protection rights |
Effective date: 20111118 |