NO841987L - Fremgangsmaate for fremstilling av pyrazolderivater med terapeutisk aktivitet - Google Patents
Fremgangsmaate for fremstilling av pyrazolderivater med terapeutisk aktivitetInfo
- Publication number
- NO841987L NO841987L NO841987A NO841987A NO841987L NO 841987 L NO841987 L NO 841987L NO 841987 A NO841987 A NO 841987A NO 841987 A NO841987 A NO 841987A NO 841987 L NO841987 L NO 841987L
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- dihydro
- pyrazol
- amine
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 title claims description 10
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 95
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- -1 methyl 4-(4,5-dihydro-1-phenyl-1H-pyrazol-3-yl)aminophenyl Chemical group 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 5
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- JYSAWHKJMZSQQJ-UHFFFAOYSA-N 2-phenyl-n-(4-phenylmethoxyphenyl)-3,4-dihydropyrazol-5-amine Chemical compound C=1C=CC=CC=1COC(C=C1)=CC=C1NC(CC1)=NN1C1=CC=CC=C1 JYSAWHKJMZSQQJ-UHFFFAOYSA-N 0.000 claims description 3
- NVELZSGOWKZXLB-UHFFFAOYSA-N 4-[(2-phenyl-3,4-dihydropyrazol-5-yl)amino]phenol Chemical compound C1=CC(O)=CC=C1NC1=NN(C=2C=CC=CC=2)CC1 NVELZSGOWKZXLB-UHFFFAOYSA-N 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- UCNIFBYJKBKXKU-UHFFFAOYSA-N ethyl n-(2-phenyl-3,4-dihydropyrazol-5-yl)-n-pyridin-3-ylcarbamate Chemical compound C=1C=CN=CC=1N(C(=O)OCC)C(CC1)=NN1C1=CC=CC=C1 UCNIFBYJKBKXKU-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- HKVKLGKZAHVSNG-UHFFFAOYSA-N n-(2-phenyl-3,4-dihydropyrazol-5-yl)pyridin-3-amine Chemical compound N=1N(C=2C=CC=CC=2)CCC=1NC1=CC=CN=C1 HKVKLGKZAHVSNG-UHFFFAOYSA-N 0.000 claims description 3
- MASICKWVQGYDLE-UHFFFAOYSA-N n-(4-chlorophenyl)-2-phenyl-3,4-dihydropyrazol-5-amine Chemical compound C1=CC(Cl)=CC=C1NC1=NN(C=2C=CC=CC=2)CC1 MASICKWVQGYDLE-UHFFFAOYSA-N 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- KRBSWTOXXVNABC-UHFFFAOYSA-N 1-n-(4,4-dimethyl-2-phenyl-3h-pyrazol-5-yl)-4-n,4-n-dimethylbenzene-1,4-diamine Chemical compound C1=CC(N(C)C)=CC=C1NC1=NN(C=2C=CC=CC=2)CC1(C)C KRBSWTOXXVNABC-UHFFFAOYSA-N 0.000 claims description 2
- HHUSESFYQVICIO-UHFFFAOYSA-N 1-n-(5,5-dimethyl-1-phenyl-4h-pyrazol-3-yl)-4-n,4-n-dimethylbenzene-1,4-diamine Chemical compound C1=CC(N(C)C)=CC=C1NC(CC1(C)C)=NN1C1=CC=CC=C1 HHUSESFYQVICIO-UHFFFAOYSA-N 0.000 claims description 2
- DJJVXSSTPDIZPM-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-n-(4-methoxyphenyl)-3,4-dihydropyrazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NN(C=2C=C(Cl)C(Cl)=CC=2)CC1 DJJVXSSTPDIZPM-UHFFFAOYSA-N 0.000 claims description 2
- USXWVGLQZZSYHS-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-(4-methoxyphenyl)-3,4-dihydropyrazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NN(C=2C=CC(Cl)=CC=2)CC1 USXWVGLQZZSYHS-UHFFFAOYSA-N 0.000 claims description 2
- BLGKIXJHZSYPIJ-UHFFFAOYSA-N 4-[(2-phenyl-3,4-dihydropyrazol-5-yl)amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NN(C=2C=CC=CC=2)CC1 BLGKIXJHZSYPIJ-UHFFFAOYSA-N 0.000 claims description 2
- HMCYKFNQAIEWDZ-UHFFFAOYSA-N 4-n,4-n-dimethyl-1-n-(2-phenyl-3,4-dihydropyrazol-5-yl)benzene-1,4-diamine Chemical compound C1=CC(N(C)C)=CC=C1NC1=NN(C=2C=CC=CC=2)CC1 HMCYKFNQAIEWDZ-UHFFFAOYSA-N 0.000 claims description 2
- XTXPJNOPMIZBNR-UHFFFAOYSA-N 5-[(2-phenyl-3,4-dihydropyrazol-5-yl)amino]-2-propylphenol Chemical compound C1=C(O)C(CCC)=CC=C1NC1=NN(C=2C=CC=CC=2)CC1 XTXPJNOPMIZBNR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- LUOFTCYLVKMSBU-UHFFFAOYSA-N n-(2,3-diphenyl-3,4-dihydropyrazol-5-yl)pyridin-3-amine Chemical compound C1C(C=2C=CC=CC=2)N(C=2C=CC=CC=2)N=C1NC1=CC=CN=C1 LUOFTCYLVKMSBU-UHFFFAOYSA-N 0.000 claims description 2
- SMCYWKAAKITYHI-UHFFFAOYSA-N n-(4-methoxyphenyl)-2-(4-methylphenyl)-3,4-dihydropyrazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NN(C=2C=CC(C)=CC=2)CC1 SMCYWKAAKITYHI-UHFFFAOYSA-N 0.000 claims description 2
- OMTIIGDGEZMMGZ-UHFFFAOYSA-N n-(4-methoxyphenyl)-2-phenyl-3,4-dihydropyrazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NN(C=2C=CC=CC=2)CC1 OMTIIGDGEZMMGZ-UHFFFAOYSA-N 0.000 claims description 2
- LHWGAISPIAHSPQ-UHFFFAOYSA-N n-(4-methoxyphenyl)-4,4-dimethyl-2-pyridin-2-yl-3h-pyrazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NN(C=2N=CC=CC=2)CC1(C)C LHWGAISPIAHSPQ-UHFFFAOYSA-N 0.000 claims description 2
- JTECDXDFFFTQRL-UHFFFAOYSA-N n-(4-methoxyphenyl)-5,5-dimethyl-1-phenyl-4h-pyrazol-3-amine Chemical compound C1=CC(OC)=CC=C1NC(CC1(C)C)=NN1C1=CC=CC=C1 JTECDXDFFFTQRL-UHFFFAOYSA-N 0.000 claims description 2
- FQMCVBCMHZJHLK-UHFFFAOYSA-N n-(4-methylphenyl)-2-phenyl-3,4-dihydropyrazol-5-amine Chemical compound C1=CC(C)=CC=C1NC1=NN(C=2C=CC=CC=2)CC1 FQMCVBCMHZJHLK-UHFFFAOYSA-N 0.000 claims description 2
- SGMNTFHBSFXTTN-UHFFFAOYSA-N n-(5,5-dimethyl-1-phenyl-4h-pyrazol-3-yl)pyridin-3-amine Chemical compound N=1N(C=2C=CC=CC=2)C(C)(C)CC=1NC1=CC=CN=C1 SGMNTFHBSFXTTN-UHFFFAOYSA-N 0.000 claims description 2
- UEJGQMVGUYMGQO-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-3,4-dihydropyrazol-5-yl]-4-methylpyridin-2-amine Chemical compound CC1=CC=NC(NC=2CCN(N=2)C=2C=CC(Cl)=CC=2)=C1 UEJGQMVGUYMGQO-UHFFFAOYSA-N 0.000 claims description 2
- NYXZFQQNWSTRNQ-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-3,4-dihydropyrazol-5-yl]pyridin-3-amine Chemical compound C1=CC(Cl)=CC=C1N1N=C(NC=2C=NC=CC=2)CC1 NYXZFQQNWSTRNQ-UHFFFAOYSA-N 0.000 claims description 2
- CCKIXYAKBMIDJJ-UHFFFAOYSA-N n-[2-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazol-5-yl]pyridin-3-amine Chemical compound FC(F)(F)C1=CC=CC(N2N=C(NC=3C=NC=CC=3)CC2)=C1 CCKIXYAKBMIDJJ-UHFFFAOYSA-N 0.000 claims description 2
- CQQIPXJVYBNYCY-UHFFFAOYSA-N n-[4-[2-(diethylamino)ethoxy]phenyl]-2-phenyl-3,4-dihydropyrazol-5-amine Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NN(C=2C=CC=CC=2)CC1 CQQIPXJVYBNYCY-UHFFFAOYSA-N 0.000 claims description 2
- KSTPTDYTHCJPBH-UHFFFAOYSA-N n-phenyl-2-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazol-5-amine Chemical compound FC(F)(F)C1=CC=CC(N2N=C(NC=3C=CC=CC=3)CC2)=C1 KSTPTDYTHCJPBH-UHFFFAOYSA-N 0.000 claims description 2
- IKYFAMICXXIQQU-UHFFFAOYSA-N 1-[4-[2-(diethylamino)ethoxy]phenyl]-3-phenyl-1-(2-phenyl-3,4-dihydropyrazol-5-yl)urea Chemical compound C1=CC(OCCN(CC)CC)=CC=C1N(C=1CCN(N=1)C=1C=CC=CC=1)C(=O)NC1=CC=CC=C1 IKYFAMICXXIQQU-UHFFFAOYSA-N 0.000 claims 1
- ATDWYZGLVJAGGM-UHFFFAOYSA-N 4,4-dimethyl-2-phenyl-3h-pyrazol-5-amine Chemical compound N1=C(N)C(C)(C)CN1C1=CC=CC=C1 ATDWYZGLVJAGGM-UHFFFAOYSA-N 0.000 claims 1
- DAIWPMZVBDFCGF-UHFFFAOYSA-N 5,5-dimethyl-1-phenyl-4h-pyrazol-3-amine Chemical compound CC1(C)CC(N)=NN1C1=CC=CC=C1 DAIWPMZVBDFCGF-UHFFFAOYSA-N 0.000 claims 1
- KNDYSPZVKKZIPJ-UHFFFAOYSA-N n,2,3-triphenyl-3,4-dihydropyrazol-5-amine Chemical compound C1C(C=2C=CC=CC=2)N(C=2C=CC=CC=2)N=C1NC1=CC=CC=C1 KNDYSPZVKKZIPJ-UHFFFAOYSA-N 0.000 claims 1
- KHCPQEUHGCYSPB-UHFFFAOYSA-N n,2-diphenyl-3,4-dihydropyrazol-5-amine Chemical compound N=1N(C=2C=CC=CC=2)CCC=1NC1=CC=CC=C1 KHCPQEUHGCYSPB-UHFFFAOYSA-N 0.000 claims 1
- WMSKURGLVVNYSY-UHFFFAOYSA-N n-(4-methoxyphenyl)-4,4-dimethyl-2-phenyl-3h-pyrazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NN(C=2C=CC=CC=2)CC1(C)C WMSKURGLVVNYSY-UHFFFAOYSA-N 0.000 claims 1
- APLUGZAWNLAQKA-UHFFFAOYSA-N n-(4-methoxyphenyl)-n-(2-phenyl-3,4-dihydropyrazol-5-yl)acetamide Chemical compound C1=CC(OC)=CC=C1N(C(C)=O)C1=NN(C=2C=CC=CC=2)CC1 APLUGZAWNLAQKA-UHFFFAOYSA-N 0.000 claims 1
- IOFBCFYOYJNMMT-UHFFFAOYSA-N n-methyl-n,2-diphenyl-3,4-dihydropyrazol-5-amine Chemical compound C=1C=CC=CC=1N(C)C(CC1)=NN1C1=CC=CC=C1 IOFBCFYOYJNMMT-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- 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
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838314111A GB8314111D0 (en) | 1983-05-21 | 1983-05-21 | Heterocyclic compound |
| GB838334283A GB8334283D0 (en) | 1983-12-22 | 1983-12-22 | Compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO841987L true NO841987L (no) | 1984-11-22 |
Family
ID=26286198
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO841987A NO841987L (no) | 1983-05-21 | 1984-05-18 | Fremgangsmaate for fremstilling av pyrazolderivater med terapeutisk aktivitet |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US4824859A (da) |
| EP (1) | EP0127371B1 (da) |
| AU (1) | AU560314B2 (da) |
| DE (1) | DE3483628D1 (da) |
| DK (1) | DK246584A (da) |
| FI (1) | FI842000A (da) |
| NO (1) | NO841987L (da) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR900100380A (el) * | 1989-05-20 | 1991-10-10 | Fisons Plc | Μέ?οδος παρασκευής αντι-φλεγμονωδών παραγώγων αμινοφενόλης. |
| FR2781147B1 (fr) | 1998-07-20 | 2000-09-15 | Oreal | Compositions pour la teinture des fibres keratiniques contenant des derives de 3-amino pyrazolines a titre de coupleur, procede de teinture et kit de teinture |
| EP2630133A1 (de) | 2010-10-22 | 2013-08-28 | Bayer Intellectual Property GmbH | Neue heterocylische verbindungen als schädlingsbekämpfungsmittel |
| BR112015009751A2 (pt) | 2012-10-31 | 2017-07-11 | Bayer Cropscience Ag | novos compostos heterocíclicos como pesticidas |
| EP2928471B1 (en) | 2012-12-06 | 2020-10-14 | Celgene Quanticel Research, Inc. | Histone demethylase inhibitors |
| US11034669B2 (en) | 2018-11-30 | 2021-06-15 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU537499B2 (en) * | 1979-07-13 | 1984-06-28 | Wellcome Foundation Limited, The | Compositions for treating inflammatory conditions |
| DE3173933D1 (en) * | 1980-12-16 | 1986-04-03 | Wellcome Found | Pyrazoline derivatives, processes for their preparation and pharmaceutical formulations containing them |
| JPS57123166A (en) * | 1980-12-16 | 1982-07-31 | Wellcome Found | Pyrazoline derivative |
| GB8303782D0 (en) * | 1983-02-11 | 1983-03-16 | Wellcome Found | Heterocyclic compounds |
| DK60684A (da) * | 1983-02-11 | 1984-08-12 | Wellcome Found | Fremgangsmaade til fremstilling af 3-(n-substitueret amino)-2-pyrazoliner og mellemprodukter anvendelige ved udoevelse af fremgangsmaaden |
| EP0178035B1 (en) * | 1984-05-12 | 1990-01-03 | FISONS plc | Anti-inflammatory 1,n-diarylpyrazol-3-amines, compositions containing them and processes for their preparation |
-
1984
- 1984-05-03 US US06/606,867 patent/US4824859A/en not_active Expired - Fee Related
- 1984-05-15 DE DE8484303262T patent/DE3483628D1/de not_active Expired - Fee Related
- 1984-05-15 EP EP84303262A patent/EP0127371B1/en not_active Expired - Lifetime
- 1984-05-16 AU AU28078/84A patent/AU560314B2/en not_active Ceased
- 1984-05-17 DK DK246584A patent/DK246584A/da not_active Application Discontinuation
- 1984-05-18 NO NO841987A patent/NO841987L/no unknown
- 1984-05-18 FI FI842000A patent/FI842000A/fi not_active Application Discontinuation
-
1989
- 1989-02-10 US US07/286,268 patent/US4956378A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU560314B2 (en) | 1987-04-02 |
| US4824859A (en) | 1989-04-25 |
| DK246584A (da) | 1984-11-22 |
| EP0127371A2 (en) | 1984-12-05 |
| EP0127371A3 (en) | 1986-01-15 |
| US4956378A (en) | 1990-09-11 |
| DK246584D0 (da) | 1984-05-17 |
| EP0127371B1 (en) | 1990-11-22 |
| FI842000A0 (fi) | 1984-05-18 |
| AU2807884A (en) | 1984-11-22 |
| FI842000A (fi) | 1984-11-22 |
| DE3483628D1 (de) | 1991-01-03 |
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