DE2221866A1 - Substituierte Anilinobenzoxazole zur prophylaktischen Anwendung gegen die Marek-Krankheit - Google Patents
Substituierte Anilinobenzoxazole zur prophylaktischen Anwendung gegen die Marek-KrankheitInfo
- Publication number
- DE2221866A1 DE2221866A1 DE19722221866 DE2221866A DE2221866A1 DE 2221866 A1 DE2221866 A1 DE 2221866A1 DE 19722221866 DE19722221866 DE 19722221866 DE 2221866 A DE2221866 A DE 2221866A DE 2221866 A1 DE2221866 A1 DE 2221866A1
- Authority
- DE
- Germany
- Prior art keywords
- trifluoromethyl
- benzoxazole
- radicals
- atoms
- anilino
- 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.)
- Pending
Links
- BFLIOKCEGCUTNH-UHFFFAOYSA-N n-phenyl-1,3-benzoxazol-2-amine Chemical class N=1C2=CC=CC=C2OC=1NC1=CC=CC=C1 BFLIOKCEGCUTNH-UHFFFAOYSA-N 0.000 title claims description 29
- 208000006758 Marek Disease Diseases 0.000 title description 2
- 230000000069 prophylactic effect Effects 0.000 title description 2
- -1 trifluoromethyl radicals Chemical class 0.000 claims description 115
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 82
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 60
- 125000001424 substituent group Chemical group 0.000 claims description 57
- 150000001875 compounds Chemical class 0.000 claims description 50
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 40
- BBVQDWDBTWSGHQ-UHFFFAOYSA-N 2-chloro-1,3-benzoxazole Chemical compound C1=CC=C2OC(Cl)=NC2=C1 BBVQDWDBTWSGHQ-UHFFFAOYSA-N 0.000 claims description 39
- 239000002904 solvent Substances 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 30
- 150000003254 radicals Chemical class 0.000 claims description 28
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 26
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 17
- 125000001153 fluoro group Chemical group F* 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 125000001246 bromo group Chemical group Br* 0.000 claims description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 12
- 150000001448 anilines Chemical class 0.000 claims description 11
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 9
- 230000003509 anti-fertility effect Effects 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 7
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 7
- 239000012312 sodium hydride Substances 0.000 claims description 7
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- ASPDJZINBYYZRU-UHFFFAOYSA-N 5-amino-2-chlorobenzotrifluoride Chemical compound NC1=CC=C(Cl)C(C(F)(F)F)=C1 ASPDJZINBYYZRU-UHFFFAOYSA-N 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000003018 immunosuppressive agent Substances 0.000 claims description 4
- 229940125721 immunosuppressive agent Drugs 0.000 claims description 4
- SLIOXWJNBCJZDC-UHFFFAOYSA-N n-(2,4-dichlorophenyl)-1,3-benzoxazol-2-amine Chemical compound ClC1=CC(Cl)=CC=C1NC1=NC2=CC=CC=C2O1 SLIOXWJNBCJZDC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 claims description 3
- GDGOJTQDJACDEP-UHFFFAOYSA-N ethyl 3-(1,3-benzoxazol-2-ylamino)benzoate Chemical compound CCOC(=O)C1=CC=CC(NC=2OC3=CC=CC=C3N=2)=C1 GDGOJTQDJACDEP-UHFFFAOYSA-N 0.000 claims description 3
- KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 claims description 2
- CEPCPXLLFXPZGW-UHFFFAOYSA-N 2,4-difluoroaniline Chemical compound NC1=CC=C(F)C=C1F CEPCPXLLFXPZGW-UHFFFAOYSA-N 0.000 claims description 2
- DRKWGMXFFCPZLW-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=CC=C1F DRKWGMXFFCPZLW-UHFFFAOYSA-N 0.000 claims description 2
- CDIDGWDGQGVCIB-UHFFFAOYSA-N 3,5-bis(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CDIDGWDGQGVCIB-UHFFFAOYSA-N 0.000 claims description 2
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 claims description 2
- YGNISOAUPSJDJE-UHFFFAOYSA-N 4-bromo-3-(trifluoromethyl)aniline Chemical compound NC1=CC=C(Br)C(C(F)(F)F)=C1 YGNISOAUPSJDJE-UHFFFAOYSA-N 0.000 claims description 2
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 claims description 2
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000006073 displacement reaction Methods 0.000 claims description 2
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 claims description 2
- 239000002871 fertility agent Substances 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- JNCZLUKLHGGFDR-UHFFFAOYSA-N n-[2-fluoro-5-(trifluoromethyl)phenyl]-1,3-benzoxazol-2-amine Chemical compound FC1=CC=C(C(F)(F)F)C=C1NC1=NC2=CC=CC=C2O1 JNCZLUKLHGGFDR-UHFFFAOYSA-N 0.000 claims description 2
- GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical compound C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- ZMCBYSBVJIMENC-UHFFFAOYSA-N tricaine Chemical compound CCOC(=O)C1=CC=CC(N)=C1 ZMCBYSBVJIMENC-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 4
- HSMPSHPWCOOUJH-UHFFFAOYSA-N anilinyl Chemical compound [NH]C1=CC=CC=C1 HSMPSHPWCOOUJH-UHFFFAOYSA-N 0.000 claims 2
- LMICINUYKWISNU-UHFFFAOYSA-N 5,6-dichloro-1,3-benzoxazole Chemical compound C1=C(Cl)C(Cl)=CC2=C1OC=N2 LMICINUYKWISNU-UHFFFAOYSA-N 0.000 claims 1
- LGHXDTHJGNCRKT-UHFFFAOYSA-N 5-nitro-2-(trifluoromethyl)aniline Chemical compound NC1=CC([N+]([O-])=O)=CC=C1C(F)(F)F LGHXDTHJGNCRKT-UHFFFAOYSA-N 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- 229940125782 compound 2 Drugs 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- PMXXPLOKBHZVAW-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-1,3-benzoxazol-2-amine Chemical compound C1=C(C)C(C)=CC=C1NC1=NC2=CC=CC=C2O1 PMXXPLOKBHZVAW-UHFFFAOYSA-N 0.000 claims 1
- SLFVYFOEHHLHDW-UHFFFAOYSA-N n-(trifluoromethyl)aniline Chemical compound FC(F)(F)NC1=CC=CC=C1 SLFVYFOEHHLHDW-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 41
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- 238000011161 development Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000001076 estrogenic effect Effects 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- WXXLGYZLPXGQLR-UHFFFAOYSA-N ethyl 4-(1,3-benzoxazol-2-ylamino)benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC1=NC2=CC=CC=C2O1 WXXLGYZLPXGQLR-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000008105 immune reaction Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- RDYFKKVHDRNHBN-UHFFFAOYSA-N n-(2,3-dimethylphenyl)-1,3-benzoxazol-2-amine Chemical compound CC1=CC=CC(NC=2OC3=CC=CC=C3N=2)=C1C RDYFKKVHDRNHBN-UHFFFAOYSA-N 0.000 description 1
- HDTOXENRGKNCGH-UHFFFAOYSA-N n-(2,5-dichlorophenyl)-1,3-benzoxazol-2-amine Chemical compound ClC1=CC=C(Cl)C(NC=2OC3=CC=CC=C3N=2)=C1 HDTOXENRGKNCGH-UHFFFAOYSA-N 0.000 description 1
- YCVGAYXIQCGTFE-UHFFFAOYSA-N n-(2-chlorophenyl)-1,3-benzoxazol-2-amine Chemical compound ClC1=CC=CC=C1NC1=NC2=CC=CC=C2O1 YCVGAYXIQCGTFE-UHFFFAOYSA-N 0.000 description 1
- NDNDQNKPPDRRCP-UHFFFAOYSA-N n-(3-chlorophenyl)-1,3-benzoxazol-2-amine Chemical compound ClC1=CC=CC(NC=2OC3=CC=CC=C3N=2)=C1 NDNDQNKPPDRRCP-UHFFFAOYSA-N 0.000 description 1
- YJUJZVVAAWUMAX-UHFFFAOYSA-N n-(3-methylphenyl)-1,3-benzoxazol-2-amine Chemical compound CC1=CC=CC(NC=2OC3=CC=CC=C3N=2)=C1 YJUJZVVAAWUMAX-UHFFFAOYSA-N 0.000 description 1
- CHPVGIPDUWHTOP-UHFFFAOYSA-N n-(3-nitrophenyl)-1,3-benzoxazol-2-amine Chemical compound [O-][N+](=O)C1=CC=CC(NC=2OC3=CC=CC=C3N=2)=C1 CHPVGIPDUWHTOP-UHFFFAOYSA-N 0.000 description 1
- DVWWGAYDBQNYTG-UHFFFAOYSA-N n-(4-chlorophenyl)-1,3-benzoxazol-2-amine Chemical compound C1=CC(Cl)=CC=C1NC1=NC2=CC=CC=C2O1 DVWWGAYDBQNYTG-UHFFFAOYSA-N 0.000 description 1
- VITGTHQUYHJKCN-UHFFFAOYSA-N n-(4-nitrophenyl)-1,3-benzoxazol-2-amine Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC1=NC2=CC=CC=C2O1 VITGTHQUYHJKCN-UHFFFAOYSA-N 0.000 description 1
- AYOOGWWGECJQPI-NSHDSACASA-N n-[(1s)-1-(5-fluoropyrimidin-2-yl)ethyl]-3-(3-propan-2-yloxy-1h-pyrazol-5-yl)imidazo[4,5-b]pyridin-5-amine Chemical compound N1C(OC(C)C)=CC(N2C3=NC(N[C@@H](C)C=4N=CC(F)=CN=4)=CC=C3N=C2)=N1 AYOOGWWGECJQPI-NSHDSACASA-N 0.000 description 1
- DOLUWBRDYALNBW-UHFFFAOYSA-N n-[4-chloro-3-(trifluoromethyl)phenyl]-1,3-benzoxazol-2-amine Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC=2OC3=CC=CC=C3N=2)=C1 DOLUWBRDYALNBW-UHFFFAOYSA-N 0.000 description 1
- KRNWWEIKCXPQDA-UHFFFAOYSA-N n-[4-chloro-3-(trifluoromethyl)phenyl]benzamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC(=O)C=2C=CC=CC=2)=C1 KRNWWEIKCXPQDA-UHFFFAOYSA-N 0.000 description 1
- LADOUOSIEVINBE-UHFFFAOYSA-N n-butyl-4-chloro-3-(trifluoromethyl)aniline Chemical compound CCCCNC1=CC=C(Cl)C(C(F)(F)F)=C1 LADOUOSIEVINBE-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14028971A | 1971-05-04 | 1971-05-04 | |
| US18854471A | 1971-10-12 | 1971-10-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2221866A1 true DE2221866A1 (de) | 1972-12-07 |
Family
ID=26838048
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722221866 Pending DE2221866A1 (de) | 1971-05-04 | 1972-05-04 | Substituierte Anilinobenzoxazole zur prophylaktischen Anwendung gegen die Marek-Krankheit |
Country Status (12)
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998040381A1 (en) * | 1997-03-14 | 1998-09-17 | Vertex Pharmaceuticals Incorporated | Inhibitors of impdh enzyme |
| US5932600A (en) * | 1997-03-14 | 1999-08-03 | Vertex Pharmaceuticals Incorporated | Inhibitors of IMPDH enzyme |
| US6344465B1 (en) | 1996-04-23 | 2002-02-05 | Vertex Pharmaceuticals, Incorporated | Inhibitors of IMPDH enzyme |
| US6541496B1 (en) | 1996-04-23 | 2003-04-01 | Vertex Pharmaceuticals Incorporated | Inhibitors of IMPDH enzyme |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1366766A1 (en) * | 1997-03-14 | 2003-12-03 | Vertex Pharmaceuticals Incorporated | Inhibitors of IMPDH enzyme |
| GB0401334D0 (en) * | 2004-01-21 | 2004-02-25 | Novartis Ag | Organic compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB873210A (en) * | 1957-04-01 | 1961-07-19 | Merck & Co Inc | Benzoxazoles |
-
1972
- 1972-05-01 IL IL39336A patent/IL39336A0/xx unknown
- 1972-05-01 CA CA140,955A patent/CA985286A/en not_active Expired
- 1972-05-02 AU AU41796/72A patent/AU4179672A/en not_active Expired
- 1972-05-03 ES ES402343A patent/ES402343A1/es not_active Expired
- 1972-05-03 BE BE782934A patent/BE782934A/xx unknown
- 1972-05-03 AT AT383072A patent/AT322549B/de not_active IP Right Cessation
- 1972-05-03 GB GB2047172A patent/GB1395641A/en not_active Expired
- 1972-05-04 NL NL7206048A patent/NL7206048A/xx unknown
- 1972-05-04 DD DD162748A patent/DD102700A5/xx unknown
- 1972-05-04 DE DE19722221866 patent/DE2221866A1/de active Pending
- 1972-05-04 FR FR7215934A patent/FR2135296B1/fr not_active Expired
-
1974
- 1974-11-18 SE SE7414459A patent/SE7414459L/xx unknown
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6344465B1 (en) | 1996-04-23 | 2002-02-05 | Vertex Pharmaceuticals, Incorporated | Inhibitors of IMPDH enzyme |
| US6541496B1 (en) | 1996-04-23 | 2003-04-01 | Vertex Pharmaceuticals Incorporated | Inhibitors of IMPDH enzyme |
| US6967214B2 (en) | 1996-04-23 | 2005-11-22 | Vertex Pharmaceuticals Incorporated | Inhibitors of IMPDH enzyme |
| US7329681B2 (en) | 1996-04-23 | 2008-02-12 | Vertex Pharmaceuticals Incorporated | Inhibitors of IMPDH enzyme |
| WO1998040381A1 (en) * | 1997-03-14 | 1998-09-17 | Vertex Pharmaceuticals Incorporated | Inhibitors of impdh enzyme |
| US5932600A (en) * | 1997-03-14 | 1999-08-03 | Vertex Pharmaceuticals Incorporated | Inhibitors of IMPDH enzyme |
| US6518291B1 (en) | 1997-03-14 | 2003-02-11 | Vertex Pharmaceuticals, Incorporated | Inhibitors of IMPDH enzyme |
Also Published As
| Publication number | Publication date |
|---|---|
| AT322549B (de) | 1975-05-26 |
| DD102700A5 (enrdf_load_stackoverflow) | 1973-12-20 |
| FR2135296B1 (enrdf_load_stackoverflow) | 1975-12-26 |
| IL39336A0 (en) | 1972-07-26 |
| GB1395641A (en) | 1975-05-29 |
| SE7414459L (enrdf_load_stackoverflow) | 1974-11-18 |
| ES402343A1 (es) | 1976-02-01 |
| BE782934A (fr) | 1972-11-03 |
| FR2135296A1 (enrdf_load_stackoverflow) | 1972-12-15 |
| CA985286A (en) | 1976-03-09 |
| AU4179672A (en) | 1973-11-08 |
| NL7206048A (enrdf_load_stackoverflow) | 1972-11-07 |
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