NL8220390A - 1-(2-benzoxazolyl)hydrazinoalkylnitrile derivaten. - Google Patents
1-(2-benzoxazolyl)hydrazinoalkylnitrile derivaten. Download PDFInfo
- Publication number
- NL8220390A NL8220390A NL8220390A NL8220390A NL8220390A NL 8220390 A NL8220390 A NL 8220390A NL 8220390 A NL8220390 A NL 8220390A NL 8220390 A NL8220390 A NL 8220390A NL 8220390 A NL8220390 A NL 8220390A
- Authority
- NL
- Netherlands
- Prior art keywords
- hydrogen
- alkyl
- oxygen
- methyl
- benzoxazolyl
- Prior art date
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- -1 2-BENZOXAZOLYL Chemical class 0.000 title claims description 61
- 150000002825 nitriles Chemical class 0.000 title claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 125000003368 amide group Chemical group 0.000 claims description 10
- 239000000460 chlorine Chemical group 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 3
- 206010061218 Inflammation Diseases 0.000 claims description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 claims description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 208000024891 symptom Diseases 0.000 claims 2
- MMWRSBUHYDTEAQ-UHFFFAOYSA-N $l^{1}-oxidanyloxymethylbenzene Chemical group [O]OCC1=CC=CC=C1 MMWRSBUHYDTEAQ-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Chemical group 0.000 claims 1
- 230000004968 inflammatory condition Effects 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 36
- 239000000243 solution Substances 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- 206010039073 rheumatoid arthritis Diseases 0.000 description 6
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- QITJGSMHKVXOFR-UHFFFAOYSA-N 1,3-benzoxazol-2-ylhydrazine Chemical compound C1=CC=C2OC(NN)=NC2=C1 QITJGSMHKVXOFR-UHFFFAOYSA-N 0.000 description 4
- 208000000104 Arthus reaction Diseases 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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- BBVQDWDBTWSGHQ-UHFFFAOYSA-N 2-chloro-1,3-benzoxazole Chemical compound C1=CC=C2OC(Cl)=NC2=C1 BBVQDWDBTWSGHQ-UHFFFAOYSA-N 0.000 description 3
- BTWPJQHMHFDOPH-UHFFFAOYSA-N 3-[amino(1,3-benzoxazol-2-yl)amino]propanenitrile Chemical compound C1=CC=C2OC(N(CCC#N)N)=NC2=C1 BTWPJQHMHFDOPH-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 208000025883 type III hypersensitivity disease Diseases 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- FLFWJIBUZQARMD-UHFFFAOYSA-N 2-mercapto-1,3-benzoxazole Chemical class C1=CC=C2OC(S)=NC2=C1 FLFWJIBUZQARMD-UHFFFAOYSA-N 0.000 description 2
- 208000024781 Immune Complex disease Diseases 0.000 description 2
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- NKKMVIVFRUYPLQ-NSCUHMNNSA-N crotononitrile Chemical compound C\C=C\C#N NKKMVIVFRUYPLQ-NSCUHMNNSA-N 0.000 description 2
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- 210000000416 exudates and transudate Anatomy 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
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- 229960002895 phenylbutazone Drugs 0.000 description 2
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
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- 230000009467 reduction Effects 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- JOXBFDPBVQGJOJ-UHFFFAOYSA-N 2,5-dichloro-1,3-benzoxazole Chemical compound ClC1=CC=C2OC(Cl)=NC2=C1 JOXBFDPBVQGJOJ-UHFFFAOYSA-N 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- WFWNMCPXXCRAMH-UHFFFAOYSA-N 2-sulfanylidene-3h-1,3-benzoxazole-5-carbonitrile Chemical compound N#CC1=CC=C2OC(S)=NC2=C1 WFWNMCPXXCRAMH-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- HJZZWSFFYPMYOI-UHFFFAOYSA-N 5,7-dimethyl-3h-1,3-benzoxazole-2-thione Chemical compound CC1=CC(C)=C2OC(S)=NC2=C1 HJZZWSFFYPMYOI-UHFFFAOYSA-N 0.000 description 1
- OPUMMEIHPXZYOP-UHFFFAOYSA-N 5-[amino(1,3-benzoxazol-2-yl)amino]pentanenitrile Chemical compound C1=CC=C2OC(N(CCCCC#N)N)=NC2=C1 OPUMMEIHPXZYOP-UHFFFAOYSA-N 0.000 description 1
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- GCVNWXZRBBCASB-UHFFFAOYSA-N 6-nitro-3h-1,3-benzoxazole-2-thione Chemical compound [O-][N+](=O)C1=CC=C2NC(=S)OC2=C1 GCVNWXZRBBCASB-UHFFFAOYSA-N 0.000 description 1
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- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
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- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical class [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000005303 weighing Methods 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
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/428—Thiazoles condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/40—Nitrogen atoms, not forming part of a nitro radical, e.g. isatin semicarbazone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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
- C07D277/82—Nitrogen atoms
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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nonwoven Fabrics (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31184381A | 1981-10-16 | 1981-10-16 | |
| US31184381 | 1981-10-16 | ||
| PCT/US1982/001296 WO1983001448A1 (en) | 1981-10-16 | 1982-09-20 | Ad1-(2-benzoxazolyl)hydrazinobdalkyl nitrile derivatives |
| US8201296 | 1982-09-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8220390A true NL8220390A (nl) | 1983-08-01 |
Family
ID=23208752
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8220390A NL8220390A (nl) | 1981-10-16 | 1982-09-20 | 1-(2-benzoxazolyl)hydrazinoalkylnitrile derivaten. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4476137A (el) |
| EP (1) | EP0091468B1 (el) |
| JP (1) | JPS58501722A (el) |
| AU (1) | AU553775B2 (el) |
| CA (1) | CA1183540A (el) |
| CH (1) | CH654573A5 (el) |
| DE (1) | DE3249054T1 (el) |
| ES (1) | ES516508A0 (el) |
| GB (1) | GB2116964B (el) |
| GR (1) | GR77022B (el) |
| IT (1) | IT1191037B (el) |
| NL (1) | NL8220390A (el) |
| NZ (1) | NZ202071A (el) |
| PH (1) | PH17577A (el) |
| PT (1) | PT75676B (el) |
| SE (1) | SE454175B (el) |
| WO (1) | WO1983001448A1 (el) |
| ZA (1) | ZA827307B (el) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3419994A1 (de) * | 1984-05-29 | 1985-12-05 | Hoechst Ag, 6230 Frankfurt | Benzoxazolyl- und benzthiazolyl-aminosaeuren, ihre herstellung und verwendung im pflanzenschutz |
| EP1283448B1 (en) | 2001-08-10 | 2008-11-05 | Samsung Electronics Co., Ltd. | Electrophotographic organophotoreceptors with charge transport compounds |
| DE60229192D1 (de) * | 2001-09-14 | 2008-11-20 | Samsung Electronics Co Ltd | Elektrophotographischer organischer Photorezeptor |
| US7118839B2 (en) | 2001-09-28 | 2006-10-10 | Samsung Electronics Co., Ltd. | Electrophotographic organophotoreceptors with novel charge transport materials |
| US6905804B2 (en) * | 2002-02-08 | 2005-06-14 | Samsung Electronics Co., Ltd. | Electrophotographic organophotoreceptors with novel charge transport materials |
| US6835513B2 (en) * | 2002-03-28 | 2004-12-28 | Samsung Electronic Co., Ltd. | Carbazole based charge transport compounds |
| US6864025B2 (en) * | 2002-03-28 | 2005-03-08 | Samsung Electronics Co., Ltd. | Sulfonyldiphenylene-based charge transport compositions |
| US6835514B2 (en) * | 2002-03-28 | 2004-12-28 | Samsung Electronics Co., Ltd. | Hydrazone-based charge transport compounds |
| US6864028B1 (en) | 2002-03-28 | 2005-03-08 | Samsung Electronics Co., Ltd. | Di-hydrazone based charge transport compounds |
| US6815133B2 (en) * | 2002-04-12 | 2004-11-09 | Samsung Electronics Co., Ltd. | Sulfonyldiphenylene based charge transport compositions |
| US6964833B2 (en) * | 2002-05-31 | 2005-11-15 | Samsung Electronics Co., Ltd. | Linked dihydrazone-based charge transport compounds |
| US6899984B2 (en) * | 2002-05-31 | 2005-05-31 | Samsung Electronics Co., Ltd. | Linked dihydrazone-based charge transport compounds |
| US7090953B2 (en) * | 2002-10-25 | 2006-08-15 | Samsung Electronics Co., Ltd. | Organophotoreceptor with a charge transport compound having an epoxy group |
| US7029812B2 (en) * | 2002-10-25 | 2006-04-18 | Samsung Electronics Co., Ltd. | Organophotoreceptor with charge transport compound having an epoxy group |
| US8476316B2 (en) | 2010-12-15 | 2013-07-02 | Olatec Industries Llc | 3-methanesulfonylpropionitrile for treating inflammation and pain |
| WO2012147904A1 (ja) * | 2011-04-27 | 2012-11-01 | 日本ゼオン株式会社 | 重合性化合物、重合性組成物、高分子、及び光学異方体 |
| CN104185621B (zh) | 2012-02-27 | 2016-09-07 | 欧拉泰克工业有限责任公司 | 用于制备3-甲磺酰基丙腈的方法 |
| JP6178412B2 (ja) | 2012-06-05 | 2017-08-09 | オラテック セラピューティクス リミティド ライアビリティ カンパニー | 炎症及び疼痛を治療するための医薬組成物 |
| CA2875198C (en) | 2012-06-11 | 2020-06-02 | Olatec Industries Llc | Compounds for treating inflammation and pain |
| US9114122B2 (en) | 2012-06-14 | 2015-08-25 | Olatec Industries Llc | Compounds for treating inflammation and pain |
| WO2014010325A1 (ja) * | 2012-07-09 | 2014-01-16 | 日本ゼオン株式会社 | 重合性化合物、重合性組成物、高分子、光学異方体、及び重合性化合物の製造方法 |
| CN105452311B (zh) * | 2013-08-22 | 2018-01-16 | 日本瑞翁株式会社 | 聚合性化合物、聚合性组合物、高分子以及光学各向异性体 |
| EP3052475B1 (en) * | 2013-10-01 | 2018-08-08 | Olatec Therapeutics LLC | Pharmaceutical use of 3-benzylsulfonylpropionitrile |
| US9999610B2 (en) | 2013-10-01 | 2018-06-19 | Olatec Therapeutics Llc | Pharmaceutical use of 3-benzylsulfonylpropionitrile |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5512427B2 (el) * | 1971-12-29 | 1980-04-02 | ||
| US3937714A (en) * | 1972-10-10 | 1976-02-10 | Eli Lilly And Company | Exchange amination process for preparing 2-hydrazinobenzothiazoles |
| JPS49135125A (el) * | 1973-05-01 | 1974-12-26 | ||
| DE2340571C3 (de) * | 1973-08-10 | 1982-01-21 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von heterocyclischen Verbindungen |
| US4178451A (en) * | 1978-07-13 | 1979-12-11 | E. R. Squibb & Sons, Inc. | 3-(Substituted hydrazino)benzisothiazole-1,1-dioxides |
| US4319026A (en) * | 1980-08-14 | 1982-03-09 | Gulf Oil Corporation | Heterocyclic-substituted hydrazides and hydrazones as plant growth regulators |
| US4387318A (en) * | 1981-06-04 | 1983-06-07 | Piezo Electric Products, Inc. | Piezoelectric fluid-electric generator |
-
1982
- 1982-09-20 GB GB08304419A patent/GB2116964B/en not_active Expired
- 1982-09-20 DE DE823249054T patent/DE3249054T1/de not_active Withdrawn
- 1982-09-20 CH CH3079/83A patent/CH654573A5/de not_active IP Right Cessation
- 1982-09-20 WO PCT/US1982/001296 patent/WO1983001448A1/en active IP Right Grant
- 1982-09-20 JP JP57503185A patent/JPS58501722A/ja active Pending
- 1982-09-20 EP EP82903204A patent/EP0091468B1/en not_active Expired
- 1982-09-20 NL NL8220390A patent/NL8220390A/nl unknown
- 1982-09-20 AU AU89993/82A patent/AU553775B2/en not_active Ceased
- 1982-10-04 NZ NZ202071A patent/NZ202071A/en unknown
- 1982-10-05 CA CA000412861A patent/CA1183540A/en not_active Expired
- 1982-10-05 ZA ZA827307A patent/ZA827307B/xx unknown
- 1982-10-07 PH PH27960A patent/PH17577A/en unknown
- 1982-10-11 GR GR69498A patent/GR77022B/el unknown
- 1982-10-14 PT PT75676A patent/PT75676B/pt unknown
- 1982-10-14 ES ES516508A patent/ES516508A0/es active Granted
- 1982-10-15 IT IT23780/82A patent/IT1191037B/it active
-
1983
- 1983-03-03 US US06/471,926 patent/US4476137A/en not_active Expired - Fee Related
- 1983-03-23 SE SE8301608A patent/SE454175B/sv not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES8401047A1 (es) | 1983-11-16 |
| IT8223780A0 (it) | 1982-10-15 |
| CH654573A5 (de) | 1986-02-28 |
| JPS58501722A (ja) | 1983-10-13 |
| SE454175B (sv) | 1988-04-11 |
| GB2116964B (en) | 1985-07-17 |
| WO1983001448A1 (en) | 1983-04-28 |
| PH17577A (en) | 1984-10-01 |
| GR77022B (el) | 1984-09-04 |
| AU553775B2 (en) | 1986-07-24 |
| ZA827307B (en) | 1983-08-31 |
| GB2116964A (en) | 1983-10-05 |
| IT1191037B (it) | 1988-02-24 |
| PT75676A (en) | 1982-11-01 |
| SE8301608D0 (sv) | 1983-03-23 |
| CA1183540A (en) | 1985-03-05 |
| NZ202071A (en) | 1985-12-13 |
| ES516508A0 (es) | 1983-11-16 |
| AU8999382A (en) | 1983-05-05 |
| US4476137A (en) | 1984-10-09 |
| DE3249054T1 (de) | 1983-11-17 |
| GB8304419D0 (en) | 1983-03-23 |
| SE8301608L (sv) | 1983-04-17 |
| PT75676B (en) | 1985-07-26 |
| EP0091468B1 (en) | 1987-08-19 |
| EP0091468A4 (en) | 1985-07-01 |
| EP0091468A1 (en) | 1983-10-19 |
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