CA2210579C - Benzene derivatives - Google Patents
Benzene derivatives Download PDFInfo
- Publication number
- CA2210579C CA2210579C CA002210579A CA2210579A CA2210579C CA 2210579 C CA2210579 C CA 2210579C CA 002210579 A CA002210579 A CA 002210579A CA 2210579 A CA2210579 A CA 2210579A CA 2210579 C CA2210579 C CA 2210579C
- Authority
- CA
- Canada
- Prior art keywords
- group
- benzene derivatives
- pharmacologically acceptable
- salts
- formula
- 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.)
- Expired - Fee Related
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- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 73
- 150000003839 salts Chemical class 0.000 claims abstract description 48
- 239000003814 drug Substances 0.000 claims abstract description 36
- 229940079593 drug Drugs 0.000 claims abstract description 28
- 208000026935 allergic disease Diseases 0.000 claims abstract description 27
- 239000012453 solvate Substances 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
- 239000004480 active ingredient Substances 0.000 claims abstract description 11
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 11
- 230000000069 prophylactic effect Effects 0.000 claims abstract description 9
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
- 230000002401 inhibitory effect Effects 0.000 claims description 27
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 206010020751 Hypersensitivity Diseases 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 5
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
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- 206010039085 Rhinitis allergic Diseases 0.000 claims description 3
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- 125000002560 nitrile group Chemical group 0.000 claims description 3
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- 150000001875 compounds Chemical class 0.000 abstract description 104
- -1 and Y = H Inorganic materials 0.000 abstract description 63
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 2
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- 229910052717 sulfur Inorganic materials 0.000 abstract description 2
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- 229910052760 oxygen Inorganic materials 0.000 abstract 1
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 16
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- QRVSWKOEFBHERX-UHFFFAOYSA-N methyl 2-[[2-[4-(4-phenylmethoxyphenoxy)phenyl]acetyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CC(C=C1)=CC=C1OC(C=C1)=CC=C1OCC1=CC=CC=C1 QRVSWKOEFBHERX-UHFFFAOYSA-N 0.000 description 4
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- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
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- 125000002350 geranyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- QHJOWSXZDCTNQX-UHFFFAOYSA-N methyl 2-(4-bromophenyl)acetate Chemical compound COC(=O)CC1=CC=C(Br)C=C1 QHJOWSXZDCTNQX-UHFFFAOYSA-N 0.000 description 1
- BDIKUZLUZLQKQA-UHFFFAOYSA-N methyl 2-[4-(4-phenylmethoxyphenoxy)phenyl]acetate Chemical compound C1=CC(CC(=O)OC)=CC=C1OC(C=C1)=CC=C1OCC1=CC=CC=C1 BDIKUZLUZLQKQA-UHFFFAOYSA-N 0.000 description 1
- VZRRIJUUMGQKAL-UHFFFAOYSA-N methyl 2-[[2-[4-(2-cyclooctyloxyphenoxy)phenyl]acetyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CC(C=C1)=CC=C1OC1=CC=CC=C1OC1CCCCCCC1 VZRRIJUUMGQKAL-UHFFFAOYSA-N 0.000 description 1
- NSHSVZKHOKFOCN-UHFFFAOYSA-N methyl 2-[[2-[4-(2-phenylmethoxyphenoxy)phenyl]acetyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CC(C=C1)=CC=C1OC1=CC=CC=C1OCC1=CC=CC=C1 NSHSVZKHOKFOCN-UHFFFAOYSA-N 0.000 description 1
- KAXUORHDXTWDAY-UHFFFAOYSA-N methyl 2-[[2-[4-(4-but-3-enoxyphenoxy)phenyl]acetyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CC(C=C1)=CC=C1OC1=CC=C(OCCC=C)C=C1 KAXUORHDXTWDAY-UHFFFAOYSA-N 0.000 description 1
- SKLYNIMCMXTLPY-UHFFFAOYSA-N methyl 2-[[2-[4-(4-butoxyphenoxy)phenyl]acetyl]amino]benzoate Chemical compound C1=CC(OCCCC)=CC=C1OC(C=C1)=CC=C1CC(=O)NC1=CC=CC=C1C(=O)OC SKLYNIMCMXTLPY-UHFFFAOYSA-N 0.000 description 1
- QNUDMLKXYNPCEP-UHFFFAOYSA-N methyl 2-[[2-[4-(4-cyclododecyloxyphenoxy)phenyl]acetyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CC(C=C1)=CC=C1OC(C=C1)=CC=C1OC1CCCCCCCCCCC1 QNUDMLKXYNPCEP-UHFFFAOYSA-N 0.000 description 1
- LTXFFEQWRVQQQB-UHFFFAOYSA-N methyl 2-[[2-[4-(4-cyclooctyloxyphenoxy)phenyl]acetyl]amino]-5-methylbenzoate Chemical compound COC(=O)C1=CC(C)=CC=C1NC(=O)CC(C=C1)=CC=C1OC(C=C1)=CC=C1OC1CCCCCCC1 LTXFFEQWRVQQQB-UHFFFAOYSA-N 0.000 description 1
- ADVUVNASBGKNFI-UHFFFAOYSA-N methyl 2-[[2-[4-(4-cyclooctyloxyphenoxy)phenyl]acetyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CC(C=C1)=CC=C1OC(C=C1)=CC=C1OC1CCCCCCC1 ADVUVNASBGKNFI-UHFFFAOYSA-N 0.000 description 1
- NEVIQXGWJUQYAV-UHFFFAOYSA-N methyl 2-[[2-[4-(4-cyclopentyloxyphenoxy)phenyl]acetyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CC(C=C1)=CC=C1OC(C=C1)=CC=C1OC1CCCC1 NEVIQXGWJUQYAV-UHFFFAOYSA-N 0.000 description 1
- OZZRCAMLQPFFAQ-UHFFFAOYSA-N methyl 2-[[2-[4-(4-hydroxyphenoxy)phenyl]acetyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CC(C=C1)=CC=C1OC1=CC=C(O)C=C1 OZZRCAMLQPFFAQ-UHFFFAOYSA-N 0.000 description 1
- XJECAPKEHSYIRN-UHFFFAOYSA-N methyl 2-[[2-[4-(4-pentan-3-yloxyphenoxy)phenyl]acetyl]amino]benzoate Chemical compound C1=CC(OC(CC)CC)=CC=C1OC(C=C1)=CC=C1CC(=O)NC1=CC=CC=C1C(=O)OC XJECAPKEHSYIRN-UHFFFAOYSA-N 0.000 description 1
- SJZQJNDWIZNZIX-UHFFFAOYSA-N methyl 2-[[2-[4-(4-phenylmethoxyphenyl)sulfanylphenyl]acetyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CC(C=C1)=CC=C1SC(C=C1)=CC=C1OCC1=CC=CC=C1 SJZQJNDWIZNZIX-UHFFFAOYSA-N 0.000 description 1
- XLFGZECQQWWDLI-UHFFFAOYSA-N methyl 2-[[2-[4-(4-propan-2-yloxyphenoxy)phenyl]acetyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CC(C=C1)=CC=C1OC1=CC=C(OC(C)C)C=C1 XLFGZECQQWWDLI-UHFFFAOYSA-N 0.000 description 1
- CRAKWCQRKSUCOG-UHFFFAOYSA-N methyl 2-[[2-[4-[4-(2-ethylbutoxy)phenoxy]phenyl]acetyl]amino]benzoate Chemical compound C1=CC(OCC(CC)CC)=CC=C1OC(C=C1)=CC=C1CC(=O)NC1=CC=CC=C1C(=O)OC CRAKWCQRKSUCOG-UHFFFAOYSA-N 0.000 description 1
- PQULHVRKLXWGQA-UHFFFAOYSA-N methyl 2-[[2-[4-[4-(2-methylpropoxy)phenoxy]phenyl]acetyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CC(C=C1)=CC=C1OC1=CC=C(OCC(C)C)C=C1 PQULHVRKLXWGQA-UHFFFAOYSA-N 0.000 description 1
- JOPAROYSRONYDJ-UHFFFAOYSA-N methyl 2-[[2-[4-[4-(2-phenoxyethoxy)phenoxy]phenyl]acetyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CC(C=C1)=CC=C1OC(C=C1)=CC=C1OCCOC1=CC=CC=C1 JOPAROYSRONYDJ-UHFFFAOYSA-N 0.000 description 1
- ADYQNZYZTUCCGJ-UHFFFAOYSA-N methyl 2-[[4-(4-cyclooctyloxyphenoxy)-3-nitrobenzoyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)C(C=C1[N+]([O-])=O)=CC=C1OC(C=C1)=CC=C1OC1CCCCCCC1 ADYQNZYZTUCCGJ-UHFFFAOYSA-N 0.000 description 1
- YOJWSXCPBKLGQJ-UHFFFAOYSA-N methyl 2-[[4-(4-cyclooctyloxyphenoxy)benzoyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)C(C=C1)=CC=C1OC(C=C1)=CC=C1OC1CCCCCCC1 YOJWSXCPBKLGQJ-UHFFFAOYSA-N 0.000 description 1
- YNWMNGBFEPMIBU-UHFFFAOYSA-N methyl 2-[[4-(4-hydroxyphenoxy)benzoyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)C(C=C1)=CC=C1OC1=CC=C(O)C=C1 YNWMNGBFEPMIBU-UHFFFAOYSA-N 0.000 description 1
- JUCWKCGQWXALBU-UHFFFAOYSA-N methyl 4-fluoro-2-[[2-[4-(3-phenylmethoxyphenoxy)phenyl]acetyl]amino]benzoate Chemical compound COC(=O)C1=CC=C(F)C=C1NC(=O)CC(C=C1)=CC=C1OC1=CC=CC(OCC=2C=CC=CC=2)=C1 JUCWKCGQWXALBU-UHFFFAOYSA-N 0.000 description 1
- RNLNRGAUPLURMK-UHFFFAOYSA-N methyl 5-chloro-2-[[2-[4-(3-phenylmethoxyphenoxy)phenyl]acetyl]amino]benzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1NC(=O)CC(C=C1)=CC=C1OC1=CC=CC(OCC=2C=CC=CC=2)=C1 RNLNRGAUPLURMK-UHFFFAOYSA-N 0.000 description 1
- CPRIIKGXMVEMSL-UHFFFAOYSA-N methyl 5-methyl-2-[[2-[4-(3-phenylmethoxyphenoxy)phenyl]acetyl]amino]benzoate Chemical compound COC(=O)C1=CC(C)=CC=C1NC(=O)CC(C=C1)=CC=C1OC1=CC=CC(OCC=2C=CC=CC=2)=C1 CPRIIKGXMVEMSL-UHFFFAOYSA-N 0.000 description 1
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- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
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- 239000002244 precipitate Substances 0.000 description 1
- GGHDAUPFEBTORZ-UHFFFAOYSA-N propane-1,1-diamine Chemical compound CCC(N)N GGHDAUPFEBTORZ-UHFFFAOYSA-N 0.000 description 1
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- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
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- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
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- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
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- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/38—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- 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
-
- 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
- A61P37/08—Antiallergic 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7/307222 | 1995-11-27 | ||
| JP30722295 | 1995-11-27 | ||
| JP8/228367 | 1996-08-29 | ||
| JP22836796 | 1996-08-29 | ||
| PCT/JP1996/003456 WO1997019910A1 (en) | 1995-11-27 | 1996-11-26 | Benzene derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2210579A1 CA2210579A1 (en) | 1997-06-05 |
| CA2210579C true CA2210579C (en) | 2003-03-11 |
Family
ID=26528211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002210579A Expired - Fee Related CA2210579C (en) | 1995-11-27 | 1996-11-26 | Benzene derivatives |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5808144A (OSRAM) |
| EP (1) | EP0806412B1 (OSRAM) |
| JP (1) | JP3117466B2 (OSRAM) |
| KR (1) | KR100309754B1 (OSRAM) |
| CN (1) | CN1081623C (OSRAM) |
| AT (1) | ATE191458T1 (OSRAM) |
| AU (1) | AU703092B2 (OSRAM) |
| CA (1) | CA2210579C (OSRAM) |
| DE (1) | DE69607597T2 (OSRAM) |
| ES (1) | ES2144786T3 (OSRAM) |
| TW (1) | TW346483B (OSRAM) |
| WO (1) | WO1997019910A1 (OSRAM) |
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|---|---|---|---|---|
| US6649656B1 (en) * | 1998-07-24 | 2003-11-18 | Teijin Limited | Anthranilic acid derivatives |
| US6627743B1 (en) * | 1999-12-03 | 2003-09-30 | Abbott Laboratories | 6-O-methylerythromycin A crystal form III |
| AU2001234089B2 (en) * | 2000-02-15 | 2005-08-11 | Teijin Limited | Cancer remedy comprising anthranilic acid derivative as active ingredient |
| GB0319124D0 (en) * | 2003-08-14 | 2003-09-17 | Smithkline Beecham Corp | Chemical compounds |
| WO2020252195A1 (en) * | 2019-06-11 | 2020-12-17 | The Wistar Institute Of Anatomy And Biology | Telomerase reverse transcriptase degraders and methods of use thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE736787A (fr) * | 1968-08-02 | 1970-01-30 | Roussel Uclaf | Dérivés de l'acide anthranilique et procédé de préparation |
| JPS60116657A (ja) * | 1983-11-30 | 1985-06-24 | Ono Pharmaceut Co Ltd | アニリン誘導体 |
| WO1993015043A1 (fr) | 1992-01-24 | 1993-08-05 | Yoshitomi Pharmaceutical Industries, Ltd. | Compose arylalkananilide et utilisation pharmaceutique |
| US5783593A (en) * | 1993-11-04 | 1998-07-21 | Abbott Laboratories | Inhibitors of squalene synthetase and protein farnesyltransferase |
-
1995
- 1995-11-27 US US08/875,284 patent/US5808144A/en not_active Expired - Fee Related
-
1996
- 1996-11-26 KR KR1019970705095A patent/KR100309754B1/ko not_active Expired - Fee Related
- 1996-11-26 DE DE69607597T patent/DE69607597T2/de not_active Expired - Fee Related
- 1996-11-26 EP EP96938545A patent/EP0806412B1/en not_active Expired - Lifetime
- 1996-11-26 AU AU75902/96A patent/AU703092B2/en not_active Ceased
- 1996-11-26 ES ES96938545T patent/ES2144786T3/es not_active Expired - Lifetime
- 1996-11-26 CN CN96191624A patent/CN1081623C/zh not_active Expired - Fee Related
- 1996-11-26 JP JP09520357A patent/JP3117466B2/ja not_active Expired - Fee Related
- 1996-11-26 TW TW085114576A patent/TW346483B/zh active
- 1996-11-26 CA CA002210579A patent/CA2210579C/en not_active Expired - Fee Related
- 1996-11-26 AT AT96938545T patent/ATE191458T1/de not_active IP Right Cessation
- 1996-11-26 WO PCT/JP1996/003456 patent/WO1997019910A1/ja not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP0806412A4 (OSRAM) | 1997-11-12 |
| ATE191458T1 (de) | 2000-04-15 |
| TW346483B (en) | 1998-12-01 |
| US5808144A (en) | 1998-09-15 |
| KR19980701699A (ko) | 1998-06-25 |
| DE69607597D1 (de) | 2000-05-11 |
| WO1997019910A1 (en) | 1997-06-05 |
| JP3117466B2 (ja) | 2000-12-11 |
| EP0806412B1 (en) | 2000-04-05 |
| CA2210579A1 (en) | 1997-06-05 |
| EP0806412A1 (en) | 1997-11-12 |
| ES2144786T3 (es) | 2000-06-16 |
| CN1173169A (zh) | 1998-02-11 |
| DE69607597T2 (de) | 2000-08-24 |
| AU703092B2 (en) | 1999-03-18 |
| KR100309754B1 (ko) | 2002-05-30 |
| AU7590296A (en) | 1997-06-19 |
| CN1081623C (zh) | 2002-03-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed | ||
| MKLA | Lapsed |
Effective date: 20081126 |