SK282458B6 - Aromatické zlúčeniny obsahujúce aminometylénovú skupinu, spôsob prípravy týchto zlúčenín, medziprodukty na ich prípravu, farmaceutický prostriedok, ktorý ich obsahuje a ich použitie - Google Patents
Aromatické zlúčeniny obsahujúce aminometylénovú skupinu, spôsob prípravy týchto zlúčenín, medziprodukty na ich prípravu, farmaceutický prostriedok, ktorý ich obsahuje a ich použitie Download PDFInfo
- Publication number
- SK282458B6 SK282458B6 SK1733-97A SK173397A SK282458B6 SK 282458 B6 SK282458 B6 SK 282458B6 SK 173397 A SK173397 A SK 173397A SK 282458 B6 SK282458 B6 SK 282458B6
- Authority
- SK
- Slovakia
- Prior art keywords
- ethylamino
- benzyl
- yloxy
- group
- bromo
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 223
- 238000002360 preparation method Methods 0.000 title claims abstract description 36
- 150000001491 aromatic compounds Chemical class 0.000 title claims description 4
- 239000000543 intermediate Substances 0.000 title abstract description 6
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 title 1
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- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 86
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- 238000000034 method Methods 0.000 claims abstract description 44
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- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
- 239000001257 hydrogen Substances 0.000 claims abstract description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 27
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 150000002148 esters Chemical class 0.000 claims abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 22
- 238000001727 in vivo Methods 0.000 claims abstract description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 17
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- PCBHHKFQNAFXJI-UHFFFAOYSA-N 3-[(2,5-dihydroxyphenyl)methylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NCC=2C(=CC=C(O)C=2)O)=C1 PCBHHKFQNAFXJI-UHFFFAOYSA-N 0.000 claims abstract description 4
- SPHGIVIKDOWDQA-UHFFFAOYSA-N 3-[(2-hydroxyphenyl)methylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NCC=2C(=CC=CC=2)O)=C1 SPHGIVIKDOWDQA-UHFFFAOYSA-N 0.000 claims abstract description 4
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- JVGAAEQVAULQRZ-UHFFFAOYSA-N 4-[(2,5-dihydroxyphenyl)methylamino]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC=C1NCC1=CC(O)=CC=C1O JVGAAEQVAULQRZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- SQSOZLKKUXKFJQ-UHFFFAOYSA-N 4-[(2,5-dihydroxyphenyl)methylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NCC1=CC(O)=CC=C1O SQSOZLKKUXKFJQ-UHFFFAOYSA-N 0.000 claims abstract description 4
- QHJPVLRQHAQHFR-UHFFFAOYSA-N 4-[(2-hydroxyphenyl)methylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NCC1=CC=CC=C1O QHJPVLRQHAQHFR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000460 chlorine Substances 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 208000002193 Pain Diseases 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 21
- 125000006239 protecting group Chemical group 0.000 claims description 21
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 18
- LNWICOUWPAYIKT-UHFFFAOYSA-N 6-[[5-chloro-2-(2-methylprop-2-enoxy)phenyl]methyl-ethylamino]pyridazine-3-carboxylic acid Chemical compound C=1C=C(C(O)=O)N=NC=1N(CC)CC1=CC(Cl)=CC=C1OCC(C)=C LNWICOUWPAYIKT-UHFFFAOYSA-N 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- VEYDRFWACUNLGJ-UHFFFAOYSA-N 6-[(5-bromo-2-hydroxyphenyl)methyl-ethylamino]pyridine-3-carboxamide Chemical compound C=1C=C(C(N)=O)C=NC=1N(CC)CC1=CC(Br)=CC=C1O VEYDRFWACUNLGJ-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000001544 thienyl group Chemical group 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- DMYLUKNFEYWGCH-UHFFFAOYSA-N pyridazine-3-carboxamide Chemical compound NC(=O)C1=CC=CN=N1 DMYLUKNFEYWGCH-UHFFFAOYSA-N 0.000 claims description 11
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- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
- PCTNAMGLSYHIPL-UHFFFAOYSA-N tin(4+) tetraazide Chemical compound [Sn+4].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-] PCTNAMGLSYHIPL-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 229960001017 tolmetin Drugs 0.000 description 1
- UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical compound NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/455—Nicotinic acids, e.g. niacin; Derivatives thereof, e.g. esters, amides
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/18—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Epidemiology (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)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicinal Preparation (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| GBGB9512475.6A GB9512475D0 (en) | 1995-06-20 | 1995-06-20 | Aromatic compounds |
| GBGB9601465.9A GB9601465D0 (en) | 1996-01-25 | 1996-01-25 | Aromatic compounds |
| PCT/GB1996/001443 WO1997000864A1 (en) | 1995-06-20 | 1996-06-17 | Aromatic compounds and pharmaceutical compositions containing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK173397A3 SK173397A3 (en) | 1998-07-08 |
| SK282458B6 true SK282458B6 (sk) | 2002-02-05 |
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| Application Number | Title | Priority Date | Filing Date |
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| SK1733-97A SK282458B6 (sk) | 1995-06-20 | 1996-06-17 | Aromatické zlúčeniny obsahujúce aminometylénovú skupinu, spôsob prípravy týchto zlúčenín, medziprodukty na ich prípravu, farmaceutický prostriedok, ktorý ich obsahuje a ich použitie |
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| EP (1) | EP0847391B1 (cs) |
| JP (1) | JP3949167B2 (cs) |
| KR (1) | KR19990023007A (cs) |
| CN (1) | CN1114598C (cs) |
| AR (1) | AR004670A1 (cs) |
| AT (1) | ATE211132T1 (cs) |
| AU (1) | AU699691B2 (cs) |
| BG (1) | BG63778B1 (cs) |
| BR (1) | BR9608908A (cs) |
| CA (1) | CA2220529A1 (cs) |
| CZ (1) | CZ290924B6 (cs) |
| DE (1) | DE69618210T2 (cs) |
| DK (1) | DK0847391T3 (cs) |
| EE (1) | EE9700342A (cs) |
| ES (1) | ES2169248T3 (cs) |
| HR (1) | HRP960289B1 (cs) |
| HU (1) | HUP9802705A3 (cs) |
| IL (1) | IL118663A (cs) |
| MX (1) | MX9710261A (cs) |
| MY (1) | MY132432A (cs) |
| NO (1) | NO311131B1 (cs) |
| NZ (1) | NZ311083A (cs) |
| PL (1) | PL324166A1 (cs) |
| PT (1) | PT847391E (cs) |
| RU (1) | RU2198878C2 (cs) |
| SK (1) | SK282458B6 (cs) |
| TW (1) | TW502026B (cs) |
| WO (1) | WO1997000864A1 (cs) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB9514160D0 (en) * | 1994-07-25 | 1995-09-13 | Zeneca Ltd | Aromatic compounds |
| GB9417532D0 (en) * | 1994-08-31 | 1994-10-19 | Zeneca Ltd | Aromatic compounds |
| TW434240B (en) | 1995-06-20 | 2001-05-16 | Zeneca Ltd | Aromatic compounds, preparation thereof and pharmaceutical composition comprising same |
| TW502026B (en) * | 1995-06-20 | 2002-09-11 | Zeneca Ltd | Aromatic compounds useful as antagonists of e-type prostaglandins, processes for the preparation thereof, pharmaceutical compositions comprising the compounds, and intermediates |
| US5834468A (en) | 1995-07-07 | 1998-11-10 | Zeneca Limited | Substituted aryl and heteroaryl compounds as E-type prostaglandin antagonists |
| JPH10507934A (ja) * | 1995-07-26 | 1998-08-04 | エヌピーエス・ファーマシウティカルズ・インコーポレイテッド | 代謝指向型グルタミン酸受容体に活性を示す化合物を同定するためのキメラ受容体および方法、ならびに神経学的障害および疾患の治療におけるそのような化合物の使用 |
| EP1000932B9 (en) * | 1997-06-27 | 2005-12-28 | Fujisawa Pharmaceutical Co., Ltd. | Aromatic ring derivatives |
| GB9903476D0 (en) | 1999-02-17 | 1999-04-07 | Zeneca Ltd | Therapeutic agents |
| CN100374416C (zh) * | 2000-04-28 | 2008-03-12 | 霍夫曼-拉罗奇有限公司 | 对(磺酰基)芳基和杂芳基类化合物 |
| SE0100873D0 (sv) * | 2001-03-13 | 2001-03-13 | Astrazeneca Ab | Method of treatment |
| EP1439837B1 (en) | 2001-10-23 | 2008-04-09 | Laboratoires Serono SA | Pyrazolidinone compounds as ligands of the prostaglandin ep2 and/or ep4 receptors |
| WO2003053923A2 (en) | 2001-12-20 | 2003-07-03 | Applied Research Systems Ars Holding N.V. | Pyrrolidine derivatives as prostaglandin modulators |
| JP4754820B2 (ja) | 2002-06-10 | 2011-08-24 | メルク セローノ ソシエテ アノニム | プロスタグランジン作動薬としてのγラクタムおよびその使用 |
| JP2006501247A (ja) * | 2002-08-30 | 2006-01-12 | バイオストラタム,インコーポレイティド | ポストamadriの後生的糖化最終産物の阻害物質 |
| ES2251866B1 (es) * | 2004-06-18 | 2007-06-16 | Laboratorios Almirall S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| CA2587318A1 (en) | 2004-12-06 | 2006-06-15 | Laboratoires Serono S.A. | Pyrrolidin-2-one derivatives for use as dp1 receptor agonists |
| ATE424386T1 (de) | 2004-12-23 | 2009-03-15 | Glaxo Group Ltd | Pyridin-verbindungen für die behandlung von prostaglandin-vermittelten krankheiten |
| US7767710B2 (en) | 2005-05-25 | 2010-08-03 | Calosyn Pharma, Inc. | Method for treating osteoarthritis |
| US20060269579A1 (en) * | 2005-05-25 | 2006-11-30 | Musculoskeletal Research Llc | Compositions for treating osteoarthritis |
| RU2442584C2 (ru) * | 2006-05-08 | 2012-02-20 | Эррера Артуро Солис | ИСПОЛЬЗОВАНИЕ НИКОТИНА, ЕГО АНАЛОГОВ, ПРЕДШЕСТВЕННИКОВ И ПРОИЗВОДНЫХ ПРИ ЛЕЧЕНИИ РАЗЛИЧНЫХ ПАТОЛОГИЧЕСКИХ ПРОЦЕССОВ, ПОДДАЮЩИХСЯ ЛЕЧЕНИЮ, ПУТЕМ ВВЕДЕНИЯ α-MSH ДЛЯ ПРОФИЛАКТИЧЕСКИХ ИЛИ ТЕРАПЕВТИЧЕСКИХ ЦЕЛЕЙ |
| EP2123273B1 (en) | 2007-02-16 | 2013-10-23 | ONO Pharmaceutical Co., Ltd. | Therapeutic agent for urinary excretion disorder |
| WO2009042854A1 (en) * | 2007-09-26 | 2009-04-02 | Musculoskeletal Research Llc | Ion-channel regulator compositions and methods of using same |
| AR081331A1 (es) | 2010-04-23 | 2012-08-08 | Cytokinetics Inc | Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos |
| AR081626A1 (es) | 2010-04-23 | 2012-10-10 | Cytokinetics Inc | Compuestos amino-piridazinicos, composiciones farmaceuticas que los contienen y uso de los mismos para tratar trastornos musculares cardiacos y esqueleticos |
| WO2011133920A1 (en) | 2010-04-23 | 2011-10-27 | Cytokinetics, Inc. | Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use |
| US20120101282A1 (en) | 2010-10-22 | 2012-04-26 | Pascal Dott | Process for the preparation of nicotinamide derivatives |
| US8759380B2 (en) | 2011-04-22 | 2014-06-24 | Cytokinetics, Inc. | Certain heterocycles, compositions thereof, and methods for their use |
| JP6200596B2 (ja) * | 2013-12-17 | 2017-09-20 | イーライ リリー アンド カンパニー | ジメチル安息香酸化合物 |
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| US3657430A (en) * | 1969-06-25 | 1972-04-18 | Merck & Co Inc | Composition and methods for treating inflammation |
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| DE2120091A1 (de) * | 1971-04-24 | 1972-11-09 | Agfa-Gevaert Ag, 5090 Leverkusen | Farbbildner für das Peroxid-Farbverstärkungs-Verfahren |
| US4350822A (en) * | 1975-03-12 | 1982-09-21 | American Cyanamid Company | Antilipidemicpara-[aryl(alkyl or alkenyl)amino]benzoic acid derivatives |
| AU510758B2 (en) * | 1976-01-19 | 1980-07-10 | The Dow Chemical Company | P-benzylaminobenzoic acids |
| US4206145A (en) * | 1976-02-11 | 1980-06-03 | Beecham Group Limited | Hypolipidaemic compounds and compositions |
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| EP0000816A1 (en) * | 1977-08-06 | 1979-02-21 | Beecham Group Plc | Substituted amino-pyridine derivatives, processes for their preparation and pharmaceutical compositions containing them |
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-
1996
- 1996-06-12 TW TW085107057A patent/TW502026B/zh not_active IP Right Cessation
- 1996-06-16 IL IL11866396A patent/IL118663A/en not_active IP Right Cessation
- 1996-06-17 CZ CZ19974110A patent/CZ290924B6/cs not_active IP Right Cessation
- 1996-06-17 PT PT96920937T patent/PT847391E/pt unknown
- 1996-06-17 BR BR9608908A patent/BR9608908A/pt not_active Application Discontinuation
- 1996-06-17 DK DK96920937T patent/DK0847391T3/da active
- 1996-06-17 RU RU98100866/04A patent/RU2198878C2/ru not_active IP Right Cessation
- 1996-06-17 HU HU9802705A patent/HUP9802705A3/hu unknown
- 1996-06-17 MX MX9710261A patent/MX9710261A/es unknown
- 1996-06-17 PL PL96324166A patent/PL324166A1/xx unknown
- 1996-06-17 JP JP50365497A patent/JP3949167B2/ja not_active Expired - Fee Related
- 1996-06-17 CN CN96196394A patent/CN1114598C/zh not_active Expired - Fee Related
- 1996-06-17 AU AU62321/96A patent/AU699691B2/en not_active Ceased
- 1996-06-17 AT AT96920937T patent/ATE211132T1/de not_active IP Right Cessation
- 1996-06-17 US US08/973,915 patent/US6100258A/en not_active Expired - Fee Related
- 1996-06-17 NZ NZ311083A patent/NZ311083A/xx unknown
- 1996-06-17 DE DE69618210T patent/DE69618210T2/de not_active Expired - Fee Related
- 1996-06-17 CA CA002220529A patent/CA2220529A1/en not_active Abandoned
- 1996-06-17 WO PCT/GB1996/001443 patent/WO1997000864A1/en not_active Application Discontinuation
- 1996-06-17 EP EP96920937A patent/EP0847391B1/en not_active Expired - Lifetime
- 1996-06-17 EE EE9700342A patent/EE9700342A/xx unknown
- 1996-06-17 KR KR1019970709477A patent/KR19990023007A/ko not_active Abandoned
- 1996-06-17 ES ES96920937T patent/ES2169248T3/es not_active Expired - Lifetime
- 1996-06-17 SK SK1733-97A patent/SK282458B6/sk unknown
- 1996-06-18 HR HR960289A patent/HRP960289B1/xx not_active IP Right Cessation
- 1996-06-19 MY MYPI96002482A patent/MY132432A/en unknown
- 1996-06-20 AR ARP960103225A patent/AR004670A1/es not_active Application Discontinuation
-
1997
- 1997-12-19 NO NO19975984A patent/NO311131B1/no unknown
-
1998
- 1998-01-09 BG BG102174A patent/BG63778B1/bg unknown
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2000
- 2000-04-03 US US09/541,306 patent/US6313148B1/en not_active Expired - Fee Related
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