IL193322A - Derivatives of 4– (3 – benzoylaminophenyl) –7,6 – domethoxy – 2– methylaminoquinazoline - Google Patents
Derivatives of 4– (3 – benzoylaminophenyl) –7,6 – domethoxy – 2– methylaminoquinazolineInfo
- Publication number
- IL193322A IL193322A IL193322A IL19332208A IL193322A IL 193322 A IL193322 A IL 193322A IL 193322 A IL193322 A IL 193322A IL 19332208 A IL19332208 A IL 19332208A IL 193322 A IL193322 A IL 193322A
- Authority
- IL
- Israel
- Prior art keywords
- salt
- compound
- hydrate
- dimethoxy
- methylaminoquinazolin
- Prior art date
Links
- WIUXQPWOYPYPPR-UHFFFAOYSA-N n-[3-[6,7-dimethoxy-2-(methylamino)quinazolin-4-yl]phenyl]benzamide Chemical class C=12C=C(OC)C(OC)=CC2=NC(NC)=NC=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC=C1 WIUXQPWOYPYPPR-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 186
- 150000003839 salts Chemical class 0.000 claims abstract description 66
- 208000003251 Pruritus Diseases 0.000 claims abstract description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
- -1 methoxy, ethoxy, 1-propoxy, 2-propoxy, methoxyethoxy, amino, methylamino, dimethylamino, ethylamino Chemical group 0.000 claims description 81
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 18
- 239000003908 antipruritic agent Substances 0.000 claims description 15
- 208000012657 Atopic disease Diseases 0.000 claims description 13
- 229940079593 drug Drugs 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 150000003431 steroids Chemical class 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 9
- 239000000739 antihistaminic agent Substances 0.000 claims description 9
- UKFCRQFQEAFNRG-UHFFFAOYSA-N 4-[[3-[6,7-dimethoxy-2-(methylamino)quinazolin-4-yl]phenyl]carbamoyl]-2-methylbenzoic acid Chemical compound C=12C=C(OC)C(OC)=CC2=NC(NC)=NC=1C(C=1)=CC=CC=1NC(=O)C1=CC=C(C(O)=O)C(C)=C1 UKFCRQFQEAFNRG-UHFFFAOYSA-N 0.000 claims description 7
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 6
- 201000008937 atopic dermatitis Diseases 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- CAWVDRBRXMORSF-UHFFFAOYSA-N 4-[[3-[6,7-dimethoxy-2-(methylamino)quinazolin-4-yl]phenyl]carbamoyl]-2-ethylbenzoic acid Chemical compound C1=C(C(O)=O)C(CC)=CC(C(=O)NC=2C=C(C=CC=2)C=2C3=CC(OC)=C(OC)C=C3N=C(NC)N=2)=C1 CAWVDRBRXMORSF-UHFFFAOYSA-N 0.000 claims description 5
- DUJAVOVVXUJZES-UHFFFAOYSA-N 2-methoxyethyl 4-[[3-[6,7-dimethoxy-2-(methylamino)quinazolin-4-yl]phenyl]carbamoyl]benzoate Chemical compound C=12C=C(OC)C(OC)=CC2=NC(NC)=NC=1C(C=1)=CC=CC=1NC(=O)C1=CC=C(C(=O)OCCOC)C=C1 DUJAVOVVXUJZES-UHFFFAOYSA-N 0.000 claims description 4
- XSVFNAFRARDFGN-UHFFFAOYSA-N 4-[[3-[6,7-dimethoxy-2-(methylamino)quinazolin-4-yl]phenyl]carbamoyl]-2-propan-2-ylbenzoic acid Chemical compound C=12C=C(OC)C(OC)=CC2=NC(NC)=NC=1C(C=1)=CC=CC=1NC(=O)C1=CC=C(C(O)=O)C(C(C)C)=C1 XSVFNAFRARDFGN-UHFFFAOYSA-N 0.000 claims description 4
- ZZQXDZSMUGHTJA-UHFFFAOYSA-N 4-n-[3-[6,7-dimethoxy-2-(methylamino)quinazolin-4-yl]phenyl]-1-n-methylbenzene-1,4-dicarboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C(=O)NC1=CC=CC(C=2C3=CC(OC)=C(OC)C=C3N=C(NC)N=2)=C1 ZZQXDZSMUGHTJA-UHFFFAOYSA-N 0.000 claims description 4
- 239000002552 dosage form Substances 0.000 claims description 4
- DKNYHLGWEWIHOZ-UHFFFAOYSA-N 2-methoxyethyl 3-[[3-[6,7-dimethoxy-2-(methylamino)quinazolin-4-yl]phenyl]carbamoyl]benzoate Chemical compound C=12C=C(OC)C(OC)=CC2=NC(NC)=NC=1C(C=1)=CC=CC=1NC(=O)C1=CC=CC(C(=O)OCCOC)=C1 DKNYHLGWEWIHOZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 238000000802 evaporation-induced self-assembly Methods 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 206010003645 Atopy Diseases 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
- 239000000203 mixture Substances 0.000 description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- 239000013078 crystal Substances 0.000 description 38
- 238000000034 method Methods 0.000 description 38
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 31
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 29
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- 238000001914 filtration Methods 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 18
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- 239000012044 organic layer Substances 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 17
- 230000006399 behavior Effects 0.000 description 17
- 239000012046 mixed solvent Substances 0.000 description 17
- 238000006748 scratching Methods 0.000 description 17
- 230000002393 scratching effect Effects 0.000 description 17
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 description 16
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- 210000004027 cell Anatomy 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- 238000005481 NMR spectroscopy Methods 0.000 description 15
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- 239000006227 byproduct Substances 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
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- 229910052763 palladium Inorganic materials 0.000 description 9
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 9
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 9
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
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- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229950001574 riboflavin phosphate Drugs 0.000 description 1
- JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 description 1
- 229960001225 rifampicin Drugs 0.000 description 1
- 230000009291 secondary effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 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
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229960005196 titanium dioxide Drugs 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 1
- DLQYXUGCCKQSRJ-UHFFFAOYSA-N tris(furan-2-yl)phosphane Chemical compound C1=COC(P(C=2OC=CC=2)C=2OC=CC=2)=C1 DLQYXUGCCKQSRJ-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/84—Nitrogen atoms
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006043273 | 2006-02-21 | ||
| PCT/JP2007/053066 WO2007097317A1 (ja) | 2006-02-21 | 2007-02-20 | ４－（３－ベンゾイルアミノフェニル）－６，７－ジメトキシ－２－メチルアミノキナゾリン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL193322A0 IL193322A0 (en) | 2009-05-04 |
| IL193322A true IL193322A (en) | 2014-04-30 |
Family
ID=42137992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL193322A IL193322A (en) | 2006-02-21 | 2008-08-07 | Derivatives of 4– (3 – benzoylaminophenyl) –7,6 – domethoxy – 2– methylaminoquinazoline |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JP4778550B2 (sr) |
| KR (1) | KR101278852B1 (sr) |
| AT (1) | ATE517875T1 (sr) |
| BR (1) | BRPI0708098B8 (sr) |
| CY (1) | CY1112554T1 (sr) |
| DK (1) | DK1992622T3 (sr) |
| ES (1) | ES2368089T3 (sr) |
| HR (1) | HRP20110604T1 (sr) |
| IL (1) | IL193322A (sr) |
| JO (1) | JO2726B1 (sr) |
| MY (1) | MY146275A (sr) |
| NZ (1) | NZ569936A (sr) |
| PT (1) | PT1992622E (sr) |
| RS (1) | RS51969B (sr) |
| RU (1) | RU2431632C2 (sr) |
| SI (1) | SI1992622T1 (sr) |
| TW (1) | TWI404709B (sr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8530654B2 (en) | 2007-02-16 | 2013-09-10 | Eisai R&D Management Co., Ltd. | Crystals, amorphous substances or salts of methyl N-[3-(6,7-dimethoxy-2-methylaminoquinazolin-4-yl) phenyl] terephthalamic acid |
| CN101687819B (zh) | 2007-08-17 | 2013-03-20 | 卫材R&D管理有限公司 | 外用剂 |
| CN101687820B (zh) | 2007-08-17 | 2012-07-25 | 卫材R&D管理有限公司 | 喹唑啉衍生物的制造方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9300059D0 (en) * | 1992-01-20 | 1993-03-03 | Zeneca Ltd | Quinazoline derivatives |
| US6262069B1 (en) * | 1997-08-29 | 2001-07-17 | Protherics Molecular Design Limited | 1-amino-7-isoquinoline derivatives as serine protease inhibitors |
| AR015966A1 (es) * | 1997-10-17 | 2001-05-30 | Smithkline Beecham Corp | Uso de un compuesto inhibidor de pde4 para la preparacion de un medicamento util para el tratamiento de prurito |
| JPH11209350A (ja) | 1998-01-26 | 1999-08-03 | Eisai Co Ltd | 含窒素複素環誘導体およびその医薬 |
| AU2005223610B2 (en) * | 2004-03-23 | 2008-05-29 | Banyu Pharmaceutical Co., Ltd. | Substituted quinazoline or pyridopyrimidine derivative |
-
2007
- 2007-02-16 TW TW096105966A patent/TWI404709B/zh not_active IP Right Cessation
- 2007-02-20 HR HR20110604T patent/HRP20110604T1/hr unknown
- 2007-02-20 AT AT07714569T patent/ATE517875T1/de active
- 2007-02-20 JO JO200752A patent/JO2726B1/en active
- 2007-02-20 ES ES07714569T patent/ES2368089T3/es active Active
- 2007-02-20 NZ NZ569936A patent/NZ569936A/en not_active IP Right Cessation
- 2007-02-20 RU RU2008137654/04A patent/RU2431632C2/ru active
- 2007-02-20 DK DK07714569.6T patent/DK1992622T3/da active
- 2007-02-20 PT PT07714569T patent/PT1992622E/pt unknown
- 2007-02-20 MY MYPI20083110A patent/MY146275A/en unknown
- 2007-02-20 KR KR1020087021869A patent/KR101278852B1/ko not_active Expired - Fee Related
- 2007-02-20 BR BRPI0708098A patent/BRPI0708098B8/pt not_active IP Right Cessation
- 2007-02-20 SI SI200730730T patent/SI1992622T1/sl unknown
- 2007-02-20 JP JP2008501719A patent/JP4778550B2/ja not_active Expired - Fee Related
- 2007-02-20 RS RS20110421A patent/RS51969B/sr unknown
-
2008
- 2008-08-07 IL IL193322A patent/IL193322A/en active IP Right Grant
-
2011
- 2011-10-10 CY CY20111100969T patent/CY1112554T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CY1112554T1 (el) | 2016-02-10 |
| RU2431632C2 (ru) | 2011-10-20 |
| JPWO2007097317A1 (ja) | 2009-07-16 |
| JO2726B1 (en) | 2013-09-15 |
| IL193322A0 (en) | 2009-05-04 |
| HRP20110604T1 (hr) | 2011-09-30 |
| RS51969B (sr) | 2012-02-29 |
| BRPI0708098B1 (pt) | 2019-08-06 |
| TW200812980A (en) | 2008-03-16 |
| PT1992622E (pt) | 2011-09-19 |
| KR20080094811A (ko) | 2008-10-24 |
| SI1992622T1 (sl) | 2011-11-30 |
| ATE517875T1 (de) | 2011-08-15 |
| HK1122025A1 (en) | 2009-05-08 |
| JP4778550B2 (ja) | 2011-09-21 |
| MY146275A (en) | 2012-07-31 |
| BRPI0708098A2 (pt) | 2011-05-17 |
| KR101278852B1 (ko) | 2013-07-01 |
| TWI404709B (zh) | 2013-08-11 |
| NZ569936A (en) | 2010-07-30 |
| BRPI0708098B8 (pt) | 2021-05-25 |
| RU2008137654A (ru) | 2010-03-27 |
| ES2368089T3 (es) | 2011-11-14 |
| DK1992622T3 (da) | 2011-09-05 |
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| KB | Patent renewed | ||
| KB | Patent renewed |