NO871879L - Fremgangsmaate for fremstilling av nye, terapeutisk aktive heterocykliske forbindelser. - Google Patents
Fremgangsmaate for fremstilling av nye, terapeutisk aktive heterocykliske forbindelser.Info
- Publication number
- NO871879L NO871879L NO871879A NO871879A NO871879L NO 871879 L NO871879 L NO 871879L NO 871879 A NO871879 A NO 871879A NO 871879 A NO871879 A NO 871879A NO 871879 L NO871879 L NO 871879L
- Authority
- NO
- Norway
- Prior art keywords
- pyrazol
- formula
- phenyl
- alkyl
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 30
- 238000002360 preparation method Methods 0.000 title claims description 12
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 71
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 24
- 150000002431 hydrogen Chemical group 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000001589 carboacyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 238000005899 aromatization reaction Methods 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- YLOCHNXWGDQLIH-UHFFFAOYSA-N 2-(1h-pyrazol-5-ylamino)phenol Chemical compound OC1=CC=CC=C1NC1=NNC=C1 YLOCHNXWGDQLIH-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- ZTBQVCJFZOKYJV-UHFFFAOYSA-N 1-benzyl-5-methyl-n-phenylpyrazol-3-amine Chemical compound N=1N(CC=2C=CC=CC=2)C(C)=CC=1NC1=CC=CC=C1 ZTBQVCJFZOKYJV-UHFFFAOYSA-N 0.000 claims description 2
- XITDNKSONMUDPZ-UHFFFAOYSA-N 1-benzyl-n-(4-methoxyphenyl)pyrazol-3-amine Chemical compound C1=CC(OC)=CC=C1NC1=NN(CC=2C=CC=CC=2)C=C1 XITDNKSONMUDPZ-UHFFFAOYSA-N 0.000 claims description 2
- YNLDOCYALPXWOV-UHFFFAOYSA-N 2-[(1-methylpyrazol-3-yl)amino]phenol Chemical compound CN1C=CC(NC=2C(=CC=CC=2)O)=N1 YNLDOCYALPXWOV-UHFFFAOYSA-N 0.000 claims description 2
- QGBMZPFZRRUQGV-UHFFFAOYSA-N 4-(1h-pyrazol-5-ylamino)phenol Chemical compound C1=CC(O)=CC=C1NC1=NNC=C1 QGBMZPFZRRUQGV-UHFFFAOYSA-N 0.000 claims description 2
- FGPOTFQRHSVAPE-UHFFFAOYSA-N 4-[(1-benzylpyrazol-3-yl)amino]phenol Chemical compound C1=CC(O)=CC=C1NC1=NN(CC=2C=CC=CC=2)C=C1 FGPOTFQRHSVAPE-UHFFFAOYSA-N 0.000 claims description 2
- ANDSTFHJMKJIKO-UHFFFAOYSA-N 4-[(1-methylpyrazol-3-yl)amino]phenol Chemical compound CN1C=CC(NC=2C=CC(O)=CC=2)=N1 ANDSTFHJMKJIKO-UHFFFAOYSA-N 0.000 claims description 2
- NKRXUTNZNMPPTN-UHFFFAOYSA-N 4-[(5-phenyl-1h-pyrazol-3-yl)amino]phenol Chemical compound C1=CC(O)=CC=C1NC1=NNC(C=2C=CC=CC=2)=C1 NKRXUTNZNMPPTN-UHFFFAOYSA-N 0.000 claims description 2
- CPVDCIXTOJGKCD-UHFFFAOYSA-N 4-[3-(4-methoxyanilino)-1H-pyrazol-5-yl]phenol Chemical compound C1=CC(OC)=CC=C1NC1=NNC(C=2C=CC(O)=CC=2)=C1 CPVDCIXTOJGKCD-UHFFFAOYSA-N 0.000 claims description 2
- SGHPAUUSPSGRQB-UHFFFAOYSA-N 4-[[1-[(4-methoxyphenyl)methyl]pyrazol-3-yl]amino]phenol Chemical compound C1=CC(OC)=CC=C1CN1N=C(NC=2C=CC(O)=CC=2)C=C1 SGHPAUUSPSGRQB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- AFMSYOHKVDOEFY-UHFFFAOYSA-N 5-methyl-n-phenyl-1h-pyrazol-3-amine Chemical compound N1C(C)=CC(NC=2C=CC=CC=2)=N1 AFMSYOHKVDOEFY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- DZODIUGJYAUAEH-UHFFFAOYSA-N n-(4-methoxyphenyl)-1-methyl-5-phenylpyrazol-3-amine Chemical compound C1=CC(OC)=CC=C1NC1=NN(C)C(C=2C=CC=CC=2)=C1 DZODIUGJYAUAEH-UHFFFAOYSA-N 0.000 claims description 2
- PVWSVMVCDCGOLW-UHFFFAOYSA-N n-(4-methoxyphenyl)-1-methylpyrazol-3-amine Chemical compound C1=CC(OC)=CC=C1NC1=NN(C)C=C1 PVWSVMVCDCGOLW-UHFFFAOYSA-N 0.000 claims description 2
- SBBYLGZCLMFIJA-UHFFFAOYSA-N n-(4-methoxyphenyl)-1h-pyrazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NNC=C1 SBBYLGZCLMFIJA-UHFFFAOYSA-N 0.000 claims description 2
- XYJWVEMIGXHRAA-UHFFFAOYSA-N n-(4-methoxyphenyl)-4,5-diphenyl-1h-pyrazol-3-amine Chemical compound C1=CC(OC)=CC=C1NC1=NNC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 XYJWVEMIGXHRAA-UHFFFAOYSA-N 0.000 claims description 2
- UEGANPRZIFWNMJ-UHFFFAOYSA-N 1-[3-(4-methoxyanilino)pyrazol-1-yl]ethanone Chemical compound C1=CC(OC)=CC=C1NC1=NN(C(C)=O)C=C1 UEGANPRZIFWNMJ-UHFFFAOYSA-N 0.000 claims 1
- BGCPLWWYPZAURQ-UHFFFAOYSA-N 5-[[5-chloro-2-(2,2,6,6-tetramethylmorpholin-4-yl)pyrimidin-4-yl]amino]-3-(3-hydroxy-3-methylbutyl)-1-methylbenzimidazol-2-one Chemical compound ClC=1C(=NC(=NC=1)N1CC(OC(C1)(C)C)(C)C)NC1=CC2=C(N(C(N2CCC(C)(C)O)=O)C)C=C1 BGCPLWWYPZAURQ-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
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- 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 9
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
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- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
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- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FGNLEIGUMSBZQP-UHFFFAOYSA-N cadaverine dihydrochloride Chemical compound Cl.Cl.NCCCCCN FGNLEIGUMSBZQP-UHFFFAOYSA-N 0.000 description 1
- HIYAVKIYRIFSCZ-UHFFFAOYSA-N calcium ionophore A23187 Natural products N=1C2=C(C(O)=O)C(NC)=CC=C2OC=1CC(C(CC1)C)OC1(C(CC1C)C)OC1C(C)C(=O)C1=CC=CN1 HIYAVKIYRIFSCZ-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 208000016644 chronic atrophic gastritis Diseases 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
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- 239000002552 dosage form Substances 0.000 description 1
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- 210000001198 duodenum Anatomy 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000013265 extended release Methods 0.000 description 1
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- 230000002349 favourable effect Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 208000007565 gingivitis Diseases 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 208000009326 ileitis Diseases 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 208000002551 irritable bowel syndrome Diseases 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 210000001589 microsome Anatomy 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- DAIALAXTILYAHE-UHFFFAOYSA-N n-(2-methoxyphenyl)-1-methylpyrazol-3-amine Chemical compound COC1=CC=CC=C1NC1=NN(C)C=C1 DAIALAXTILYAHE-UHFFFAOYSA-N 0.000 description 1
- IIMMPVUXXYHFFW-UHFFFAOYSA-N n-(2-methoxyphenyl)-1h-pyrazol-5-amine Chemical compound COC1=CC=CC=C1NC1=CC=NN1 IIMMPVUXXYHFFW-UHFFFAOYSA-N 0.000 description 1
- HVAMZIRCNOJSMJ-UHFFFAOYSA-N n-(4-methoxyphenyl)-3-phenylprop-2-ynethioamide Chemical compound C1=CC(OC)=CC=C1NC(=S)C#CC1=CC=CC=C1 HVAMZIRCNOJSMJ-UHFFFAOYSA-N 0.000 description 1
- XNKUXEFTNCRWAX-UHFFFAOYSA-N n-(4-methoxyphenyl)-5-methyl-1h-pyrazol-3-amine Chemical compound C1=CC(OC)=CC=C1NC1=NNC(C)=C1 XNKUXEFTNCRWAX-UHFFFAOYSA-N 0.000 description 1
- 210000000440 neutrophil Anatomy 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 210000003200 peritoneal cavity Anatomy 0.000 description 1
- 210000003024 peritoneal macrophage Anatomy 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000003127 radioimmunoassay Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003345 scintillation counting Methods 0.000 description 1
- 210000001625 seminal vesicle Anatomy 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 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
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000011200 topical administration Methods 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
- 238000001665 trituration Methods 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 201000010653 vesiculitis Diseases 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or 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
- C07D231/38—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB868611102A GB8611102D0 (en) | 1986-05-07 | 1986-05-07 | Heterocyclic compounds |
| GB868630906A GB8630906D0 (en) | 1986-12-24 | 1986-12-24 | Heterocyclic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO871879D0 NO871879D0 (no) | 1987-05-06 |
| NO871879L true NO871879L (no) | 1987-11-09 |
Family
ID=26290729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO871879A NO871879L (no) | 1986-05-07 | 1987-05-06 | Fremgangsmaate for fremstilling av nye, terapeutisk aktive heterocykliske forbindelser. |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4803216A (de) |
| EP (1) | EP0248523B1 (de) |
| KR (1) | KR870011101A (de) |
| AT (1) | AT390732B (de) |
| AU (1) | AU595602B2 (de) |
| CA (1) | CA1305157C (de) |
| DE (1) | DE3773746D1 (de) |
| DK (1) | DK231687A (de) |
| FI (1) | FI871974L (de) |
| IL (1) | IL82421A0 (de) |
| NO (1) | NO871879L (de) |
| NZ (1) | NZ220214A (de) |
| PT (1) | PT84831B (de) |
Families Citing this family (30)
| 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. |
| DE4234886A1 (de) * | 1992-10-16 | 1994-04-21 | Wella Ag | Neue N-Phenylaminopyrazol-Derivate sowie Mittel und Verfahren zur Färbung von Haaren |
| GB9312853D0 (en) * | 1993-06-22 | 1993-08-04 | Euro Celtique Sa | Chemical compounds |
| US5500439A (en) * | 1993-12-09 | 1996-03-19 | Alteon Inc. | Aminopyrazoles |
| US5591776A (en) * | 1994-06-24 | 1997-01-07 | Euro-Celtique, S.A. | Pheynl or benzyl-substituted rolipram-based compounds for and method of inhibiting phosphodiesterase IV |
| MX9700068A (es) * | 1994-06-24 | 1997-12-31 | Euro Celtique Sa | Compuestos y metodo para inhibir a la fosfodiesterasa iv. |
| US5922751A (en) * | 1994-06-24 | 1999-07-13 | Euro-Celtique, S.A. | Aryl pyrazole compound for inhibiting phosphodiesterase IV and methods of using same |
| CA2206287C (en) * | 1994-12-13 | 2001-03-20 | Mark Chasin | Aryl thioxanthines |
| US6025361A (en) * | 1994-12-13 | 2000-02-15 | Euro-Celtique, S.A. | Trisubstituted thioxanthines |
| CA2206804C (en) * | 1994-12-13 | 2002-03-19 | Euro-Celtique, S.A. | Trisubstituted thioxanthines |
| US6166041A (en) * | 1995-10-11 | 2000-12-26 | Euro-Celtique, S.A. | 2-heteroaryl and 2-heterocyclic benzoxazoles as PDE IV inhibitors for the treatment of asthma |
| US6075016A (en) * | 1996-04-10 | 2000-06-13 | Euro-Celtique S.A. | 6,5-fused aromatic ring systems having enhanced phosphodiesterase IV inhibitory activity |
| US5864037A (en) * | 1996-06-06 | 1999-01-26 | Euro-Celtique, S.A. | Methods for the synthesis of chemical compounds having PDE-IV inhibitory activity |
| US5744473A (en) * | 1996-09-16 | 1998-04-28 | Euro-Celtique, S.A. | PDE IV inhibitors: "bis-compounds" |
| EP1554572B1 (de) | 2001-07-25 | 2009-10-14 | Raptor Pharmaceutical Inc. | Zusammensetzungen und verfahren zur modulation des transports durch die blut-hirn-schranke |
| WO2004076414A2 (en) * | 2003-02-27 | 2004-09-10 | Smithkline Beecham Corporation | Novel compounds |
| GB0326601D0 (en) * | 2003-11-14 | 2003-12-17 | Novartis Ag | Organic compounds |
| DK1889198T3 (da) | 2005-04-28 | 2015-02-09 | Proteus Digital Health Inc | Farma-informatiksystem |
| JO3019B1 (ar) | 2006-04-19 | 2016-09-05 | Janssen Pharmaceutica Nv | ثلاثي مستبدل 4،2،1-ثلاثي زولات |
| KR20090071598A (ko) | 2006-09-18 | 2009-07-01 | 랩터 파마슈티컬 인코포레이티드 | 수용체 결합 단백질(ｒａｐ)-접합체 투여에 의한 간 질환의 치료 |
| JO2784B1 (en) | 2007-10-18 | 2014-03-15 | شركة جانسين فارماسوتيكا ان. في | 5,3,1 - Triazole substitute derivative |
| ES2424023T3 (es) | 2007-10-18 | 2013-09-26 | Janssen Pharmaceutica N.V. | 1,2,4-triazoles trisustituidos |
| MY152486A (en) | 2008-03-19 | 2014-10-15 | Janssen Pharmaceutica Nv | Trisubstituted 1,2,4 - triazoles as nicotinic acetylcholine receptor modulators |
| US8779158B2 (en) * | 2008-05-09 | 2014-07-15 | Janssen Pharmaceutica Nv | Trisubstituted pyrazoles as acetylcholine receptor modulators |
| WO2010095940A2 (en) | 2009-02-20 | 2010-08-26 | To-Bbb Holding B.V. | Glutathione-based drug delivery system |
| TWI556839B (zh) | 2009-05-06 | 2016-11-11 | 研究室護膚股份有限公司 | 包含活性劑－磷酸鈣粒子複合物之皮膚遞送組成物及其使用方法 |
| EP2491024B1 (de) | 2009-09-17 | 2013-11-20 | Janssen Pharmaceutica N.V. | Substituierte n-Phenyl-1-(4-pyridinyl)-1h-pyrazol-3-amine |
| US20120077778A1 (en) | 2010-09-29 | 2012-03-29 | Andrea Bourdelais | Ladder-Frame Polyether Conjugates |
| US9828351B2 (en) * | 2014-06-26 | 2017-11-28 | Monash University | Enzyme interacting agents |
| AU2019217094B2 (en) * | 2018-02-07 | 2023-04-06 | Industry-Academic Cooperation Foundation, Yonsei University | Compounds for inhibiting TNIK and medical uses thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD211343A1 (de) * | 1982-11-08 | 1984-07-11 | Univ Ernst Moritz Arndt | Verfahren zur synthese von pyrazolen |
| ATE49198T1 (de) * | 1984-05-12 | 1990-01-15 | Fisons Plc | Antiinflammatorische 1,n-diarylpyrazol-3-amine, deren zusammensetzungen und verfahren zu deren herstellung. |
-
1987
- 1987-04-27 EP EP87303666A patent/EP0248523B1/de not_active Expired - Lifetime
- 1987-04-27 DE DE8787303666T patent/DE3773746D1/de not_active Expired - Fee Related
- 1987-05-05 IL IL82421A patent/IL82421A0/xx unknown
- 1987-05-05 FI FI871974A patent/FI871974L/fi not_active IP Right Cessation
- 1987-05-05 US US07/046,656 patent/US4803216A/en not_active Expired - Fee Related
- 1987-05-06 DK DK231687A patent/DK231687A/da not_active Application Discontinuation
- 1987-05-06 NZ NZ220214A patent/NZ220214A/xx unknown
- 1987-05-06 CA CA000536506A patent/CA1305157C/en not_active Expired - Fee Related
- 1987-05-06 NO NO871879A patent/NO871879L/no unknown
- 1987-05-07 AU AU72584/87A patent/AU595602B2/en not_active Ceased
- 1987-05-07 PT PT84831A patent/PT84831B/pt not_active IP Right Cessation
- 1987-05-07 KR KR870004448A patent/KR870011101A/ko not_active Withdrawn
- 1987-11-03 AT AT0290487A patent/AT390732B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK231687D0 (da) | 1987-05-06 |
| CA1305157C (en) | 1992-07-14 |
| NO871879D0 (no) | 1987-05-06 |
| US4803216A (en) | 1989-02-07 |
| DE3773746D1 (en) | 1991-11-21 |
| AU595602B2 (en) | 1990-04-05 |
| PT84831B (pt) | 1990-02-08 |
| PT84831A (en) | 1987-06-01 |
| EP0248523B1 (de) | 1991-10-16 |
| ATA290487A (de) | 1989-12-15 |
| FI871974A0 (fi) | 1987-05-05 |
| AT390732B (de) | 1990-06-25 |
| EP0248523A1 (de) | 1987-12-09 |
| NZ220214A (en) | 1990-06-26 |
| DK231687A (da) | 1987-11-08 |
| KR870011101A (ko) | 1987-12-21 |
| IL82421A0 (en) | 1987-11-30 |
| FI871974A7 (fi) | 1987-11-08 |
| FI871974L (fi) | 1987-11-08 |
| AU7258487A (en) | 1987-11-12 |
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