DE3444135A1 - Selenoxide, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate - Google Patents
Selenoxide, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparateInfo
- Publication number
- DE3444135A1 DE3444135A1 DE19843444135 DE3444135A DE3444135A1 DE 3444135 A1 DE3444135 A1 DE 3444135A1 DE 19843444135 DE19843444135 DE 19843444135 DE 3444135 A DE3444135 A DE 3444135A DE 3444135 A1 DE3444135 A1 DE 3444135A1
- Authority
- DE
- Germany
- Prior art keywords
- benzisoselenazol
- oxide
- hydrogen
- formula
- methoxy
- 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.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 title claims abstract description 7
- 239000000825 pharmaceutical preparation Substances 0.000 title claims abstract description 7
- 150000003962 selenoxides Chemical class 0.000 title abstract 2
- NMHUEKTZORYKHX-UHFFFAOYSA-N 1$l^{4},2-benzoselenazole 1-oxide Chemical class C1=CC=C2[Se](=O)N=CC2=C1 NMHUEKTZORYKHX-UHFFFAOYSA-N 0.000 claims abstract description 7
- -1 methylenedioxy Chemical group 0.000 claims description 53
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- ZIJTYIRGFVHPHZ-UHFFFAOYSA-N selenium oxide(seo) Chemical class [Se]=O ZIJTYIRGFVHPHZ-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical group [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 229910001415 sodium ion Inorganic materials 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- SBTLFLABILGUMK-UHFFFAOYSA-N 1-oxo-2-phenyl-1$l^{4},2-benzoselenazol-3-one Chemical compound O=[Se]1C2=CC=CC=C2C(=O)N1C1=CC=CC=C1 SBTLFLABILGUMK-UHFFFAOYSA-N 0.000 description 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 101710172562 Cobra venom factor Proteins 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- ILROLYQPRYHHFG-UHFFFAOYSA-N 1-$l^{1}-oxidanylprop-2-en-1-one Chemical group [O]C(=O)C=C ILROLYQPRYHHFG-UHFFFAOYSA-N 0.000 description 1
- KDYMXOMOFITDSH-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-1,2-benzoselenazol-3-one Chemical compound C1=C2OCOC2=CC(N2C(C3=CC=CC=C3[se]2)=O)=C1 KDYMXOMOFITDSH-UHFFFAOYSA-N 0.000 description 1
- NNBKJFDJYNBTBP-UHFFFAOYSA-N 2-(3-chlorophenyl)-1,2-benzoselenazol-3-one Chemical compound ClC1=CC=CC(N2C(C3=CC=CC=C3[se]2)=O)=C1 NNBKJFDJYNBTBP-UHFFFAOYSA-N 0.000 description 1
- JTJRNFGGGCLXSL-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,2-benzoselenazol-3-one Chemical compound FC1=CC=CC(N2C(C3=CC=CC=C3[se]2)=O)=C1 JTJRNFGGGCLXSL-UHFFFAOYSA-N 0.000 description 1
- CMIGAQUBRPEFDM-UHFFFAOYSA-N 2-(4-fluorophenyl)-1,2-benzoselenazol-3-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C2=CC=CC=C2[se]1 CMIGAQUBRPEFDM-UHFFFAOYSA-N 0.000 description 1
- UFNLROFKXBUCTG-UHFFFAOYSA-N 2-(4-methoxyphenyl)-1,2-benzoselenazol-3-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)C2=CC=CC=C2[se]1 UFNLROFKXBUCTG-UHFFFAOYSA-N 0.000 description 1
- TUVKZFWBFHCOGE-UHFFFAOYSA-N 2-(4-methylphenyl)-1,2-benzoselenazol-3-one Chemical compound C1=CC(C)=CC=C1N1C(=O)C2=CC=CC=C2[se]1 TUVKZFWBFHCOGE-UHFFFAOYSA-N 0.000 description 1
- JWLXOHUMYJGZPC-UHFFFAOYSA-N 2-(4-nitrophenyl)-1,2-benzoselenazol-3-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1C(=O)C2=CC=CC=C2[se]1 JWLXOHUMYJGZPC-UHFFFAOYSA-N 0.000 description 1
- NAOYSRBUEYWQNL-UHFFFAOYSA-N 2-benzyl-1,2-benzoselenazol-3-one Chemical compound [se]1C2=CC=CC=C2C(=O)N1CC1=CC=CC=C1 NAOYSRBUEYWQNL-UHFFFAOYSA-N 0.000 description 1
- JLRQSOFPTUQKOB-UHFFFAOYSA-N 2-benzyl-1-oxo-1lambda4,2-benzoselenazol-3-one Chemical compound C(C1=CC=CC=C1)N1[Se](C2=C(C1=O)C=CC=C2)=O JLRQSOFPTUQKOB-UHFFFAOYSA-N 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GQYKHKFCKDBFLA-UHFFFAOYSA-N 4-(3-oxo-1,2-benzoselenazol-2-yl)benzonitrile Chemical compound [se]1C2=CC=CC=C2C(=O)N1C1=CC=C(C#N)C=C1 GQYKHKFCKDBFLA-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- DFJATHACFJXJCK-UHFFFAOYSA-N 5-chloro-2-phenyl-1,2-benzoselenazol-3-one Chemical compound O=C1C2=CC(Cl)=CC=C2[se]N1C1=CC=CC=C1 DFJATHACFJXJCK-UHFFFAOYSA-N 0.000 description 1
- VYFOBZAIPIKAPR-UHFFFAOYSA-N 7-methoxy-2-phenyl-1,2-benzoselenazol-3-one Chemical compound COC1=CC=CC(C2=O)=C1[se]N2C1=CC=CC=C1 VYFOBZAIPIKAPR-UHFFFAOYSA-N 0.000 description 1
- DYEFUKCXAQOFHX-UHFFFAOYSA-N Ebselen Chemical compound [se]1C2=CC=CC=C2C(=O)N1C1=CC=CC=C1 DYEFUKCXAQOFHX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- UBKDBPVPAMXHLJ-UHFFFAOYSA-N [Se]=O.[Se]1(N=CC2=C1C=CC=C2)=O Chemical class [Se]=O.[Se]1(N=CC2=C1C=CC=C2)=O UBKDBPVPAMXHLJ-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Chemical group 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D293/00—Heterocyclic compounds containing rings having nitrogen and selenium or nitrogen and tellurium, with or without oxygen or sulfur atoms, as the ring hetero atoms
- C07D293/10—Heterocyclic compounds containing rings having nitrogen and selenium or nitrogen and tellurium, with or without oxygen or sulfur atoms, as the ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D293/12—Selenazoles; Hydrogenated selenazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843444135 DE3444135A1 (de) | 1984-12-04 | 1984-12-04 | Selenoxide, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843444135 DE3444135A1 (de) | 1984-12-04 | 1984-12-04 | Selenoxide, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3444135A1 true DE3444135A1 (de) | 1986-06-05 |
| DE3444135C2 DE3444135C2 (enExample) | 1992-12-10 |
Family
ID=6251831
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843444135 Granted DE3444135A1 (de) | 1984-12-04 | 1984-12-04 | Selenoxide, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3444135A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0701554B1 (fr) * | 1994-04-07 | 2001-06-27 | OXIS Isle of Man, Limited | Nouveaux composes de structure benzisoselen-azolin et -azine, leur procede de preparation et leurs applications therapeutiques |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3027075A1 (de) * | 1980-07-17 | 1982-02-18 | A. Nattermann & Cie GmbH, 5000 Köln | Benzisoselenazolone, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
-
1984
- 1984-12-04 DE DE19843444135 patent/DE3444135A1/de active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3027075A1 (de) * | 1980-07-17 | 1982-02-18 | A. Nattermann & Cie GmbH, 5000 Köln | Benzisoselenazolone, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| DE3027075C2 (enExample) * | 1980-07-17 | 1989-05-18 | A. Nattermann & Cie Gmbh, 5000 Koeln, De |
Non-Patent Citations (2)
| Title |
|---|
| Biochem. Pharmacol. 33(1984), 3235-3239 * |
| Biochem. Pharmacol. 33(1984), 3241-3245 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0701554B1 (fr) * | 1994-04-07 | 2001-06-27 | OXIS Isle of Man, Limited | Nouveaux composes de structure benzisoselen-azolin et -azine, leur procede de preparation et leurs applications therapeutiques |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3444135C2 (enExample) | 1992-12-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |