FI69452C - Foerfarande foer framstaellning av nya terapeutiskt anvaendbara oxazolinfoereningar - Google Patents
Foerfarande foer framstaellning av nya terapeutiskt anvaendbara oxazolinfoereningar Download PDFInfo
- Publication number
- FI69452C FI69452C FI803940A FI803940A FI69452C FI 69452 C FI69452 C FI 69452C FI 803940 A FI803940 A FI 803940A FI 803940 A FI803940 A FI 803940A FI 69452 C FI69452 C FI 69452C
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- Finland
- Prior art keywords
- compound
- formula
- alkyl
- hydrogen
- mixture
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- 230000001225 therapeutic effect Effects 0.000 title 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 43
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000000460 chlorine Chemical group 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000003504 2-oxazolinyl group Chemical class O1C(=NCC1)* 0.000 claims 1
- 101150026868 CHS1 gene Proteins 0.000 claims 1
- 230000006750 UV protection Effects 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 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 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- FRGAJCJAEQEGQB-UHFFFAOYSA-N 2,2-dimethyl-3-phenylazirine Chemical compound CC1(C)N=C1C1=CC=CC=C1 FRGAJCJAEQEGQB-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000008103 glucose Substances 0.000 description 5
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 4
- ZRKUQAXOMUSPEH-UHFFFAOYSA-N 4-(methylamino)benzaldehyde Chemical compound CNC1=CC=C(C=O)C=C1 ZRKUQAXOMUSPEH-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- -1 benzene Chemical class 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 206010012601 diabetes mellitus Diseases 0.000 description 4
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- 239000007788 liquid Substances 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- AIPTVGGEVILGAD-UHFFFAOYSA-N n-[4-(2,2-dimethyl-4-phenyl-5h-1,3-oxazol-5-yl)phenyl]-n-methylformamide Chemical compound C1=CC(N(C=O)C)=CC=C1C1C(C=2C=CC=CC=2)=NC(C)(C)O1 AIPTVGGEVILGAD-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- VATYWCRQDJIRAI-UHFFFAOYSA-N p-aminobenzaldehyde Chemical compound NC1=CC=C(C=O)C=C1 VATYWCRQDJIRAI-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- DGPYFXUBTULRPD-UHFFFAOYSA-N 2-[4-(dimethylamino)phenyl]-2-hydroxy-1-phenylethanone Chemical compound C1=CC(N(C)C)=CC=C1C(O)C(=O)C1=CC=CC=C1 DGPYFXUBTULRPD-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 102000004877 Insulin Human genes 0.000 description 3
- 108090001061 Insulin Proteins 0.000 description 3
- 241000699670 Mus sp. 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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- SOLBSNQBVLAREX-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]-2-hydroxy-2-phenylethanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C(O)C1=CC=CC=C1 SOLBSNQBVLAREX-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
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- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- ASBJTGLELWWPJD-UHFFFAOYSA-N 2,2-dimethyl-3-(2-methylphenyl)azirine Chemical compound CC1=CC=CC=C1C1=NC1(C)C ASBJTGLELWWPJD-UHFFFAOYSA-N 0.000 description 1
- QBMLQURJJUWYBN-UHFFFAOYSA-N 2,2-dimethyl-4-phenyl-5h-1,3-oxazole Chemical compound CC1(C)OCC(C=2C=CC=CC=2)=N1 QBMLQURJJUWYBN-UHFFFAOYSA-N 0.000 description 1
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- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- HZDLPUAYNCNDOM-UHFFFAOYSA-N 3-(2-chlorophenyl)-2,2-dimethylazirine Chemical compound CC1(C)N=C1C1=CC=CC=C1Cl HZDLPUAYNCNDOM-UHFFFAOYSA-N 0.000 description 1
- VZYQBTCRWXHKKA-UHFFFAOYSA-N 3-(3-chlorophenyl)-2,2-dimethylazirine Chemical compound CC1(C)N=C1C1=CC=CC(Cl)=C1 VZYQBTCRWXHKKA-UHFFFAOYSA-N 0.000 description 1
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- DVCKFBTUXYEUIO-UHFFFAOYSA-N 4-(2,2-dimethyl-4-phenyl-5h-1,3-oxazol-5-yl)-n,n,3,5-tetramethylaniline Chemical compound CC1=CC(N(C)C)=CC(C)=C1C1C(C=2C=CC=CC=2)=NC(C)(C)O1 DVCKFBTUXYEUIO-UHFFFAOYSA-N 0.000 description 1
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- HDOZLDYBGNJMMZ-UHFFFAOYSA-N 4-(dipropylamino)benzaldehyde Chemical compound CCCN(CCC)C1=CC=C(C=O)C=C1 HDOZLDYBGNJMMZ-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
- 229910052573 porcelain Inorganic materials 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 1
- 229960001052 streptozocin Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000002723 toxicity assay Methods 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 210000003462 vein Anatomy 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
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1141079 | 1979-12-21 | ||
| CH1141079 | 1979-12-21 | ||
| CH785680 | 1980-10-21 | ||
| CH785680 | 1980-10-21 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI803940L FI803940L (fi) | 1981-06-22 |
| FI69452B FI69452B (fi) | 1985-10-31 |
| FI69452C true FI69452C (fi) | 1986-02-10 |
Family
ID=25702346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI803940A FI69452C (fi) | 1979-12-21 | 1980-12-17 | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara oxazolinfoereningar |
Country Status (29)
| Country | Link |
|---|---|
| US (2) | US4317914A (cs) |
| EP (1) | EP0031562B1 (cs) |
| KR (2) | KR840002303B1 (cs) |
| AR (1) | AR230052A1 (cs) |
| AU (1) | AU540643B2 (cs) |
| BR (1) | BR8008189A (cs) |
| CA (1) | CA1169074A (cs) |
| CS (1) | CS221960B2 (cs) |
| CU (1) | CU21295A3 (cs) |
| DE (2) | DE3067063D1 (cs) |
| DK (1) | DK149771B (cs) |
| ES (1) | ES8203355A1 (cs) |
| FI (1) | FI69452C (cs) |
| FR (1) | FR2471978A1 (cs) |
| GB (1) | GB2066250B (cs) |
| GR (1) | GR72809B (cs) |
| HU (1) | HU182258B (cs) |
| IE (1) | IE51008B1 (cs) |
| IL (1) | IL61713A (cs) |
| IT (1) | IT1134431B (cs) |
| LU (1) | LU83017A1 (cs) |
| MC (1) | MC1366A1 (cs) |
| MY (1) | MY8500271A (cs) |
| NL (1) | NL8006595A (cs) |
| NO (1) | NO154011C (cs) |
| NZ (1) | NZ195830A (cs) |
| PT (1) | PT72249B (cs) |
| SE (1) | SE8009015L (cs) |
| ZW (1) | ZW28780A1 (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5952360A (en) * | 1997-08-28 | 1999-09-14 | Eli Lilly And Company | Method for treating neuropathic pain |
| US5942530A (en) * | 1997-08-28 | 1999-08-24 | Eli Lilly And Company | Method for treating pain |
| DE102010030688A1 (de) | 2010-06-30 | 2012-01-05 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Dicyanopyridine und ihre Verwendung |
-
1980
- 1980-11-17 CA CA000364793A patent/CA1169074A/en not_active Expired
- 1980-11-19 CS CS807848A patent/CS221960B2/cs unknown
- 1980-11-24 IT IT26191/80A patent/IT1134431B/it active
- 1980-11-26 ZW ZW287/80A patent/ZW28780A1/xx unknown
- 1980-12-03 NL NL8006595A patent/NL8006595A/nl not_active Application Discontinuation
- 1980-12-12 US US06/215,965 patent/US4317914A/en not_active Expired - Fee Related
- 1980-12-15 BR BR8008189A patent/BR8008189A/pt unknown
- 1980-12-15 HU HU802991A patent/HU182258B/hu unknown
- 1980-12-15 NZ NZ195830A patent/NZ195830A/en unknown
- 1980-12-15 IL IL61713A patent/IL61713A/xx unknown
- 1980-12-16 AU AU65420/80A patent/AU540643B2/en not_active Ceased
- 1980-12-17 FI FI803940A patent/FI69452C/fi not_active IP Right Cessation
- 1980-12-18 FR FR8026922A patent/FR2471978A1/fr active Granted
- 1980-12-18 MC MC801490A patent/MC1366A1/xx unknown
- 1980-12-19 NO NO803890A patent/NO154011C/no unknown
- 1980-12-19 CU CU8035394A patent/CU21295A3/es unknown
- 1980-12-19 SE SE8009015A patent/SE8009015L/xx not_active Application Discontinuation
- 1980-12-19 DK DK545980AA patent/DK149771B/da not_active Application Discontinuation
- 1980-12-19 LU LU83017A patent/LU83017A1/de unknown
- 1980-12-19 PT PT72249A patent/PT72249B/pt unknown
- 1980-12-19 AR AR283734A patent/AR230052A1/es active
- 1980-12-19 GB GB8040801A patent/GB2066250B/en not_active Expired
- 1980-12-19 DE DE8080108065T patent/DE3067063D1/de not_active Expired
- 1980-12-19 IE IE2682/80A patent/IE51008B1/en unknown
- 1980-12-19 DE DE19803048169 patent/DE3048169A1/de not_active Withdrawn
- 1980-12-19 EP EP80108065A patent/EP0031562B1/de not_active Expired
- 1980-12-20 KR KR1019800004867A patent/KR840002303B1/ko not_active Expired
- 1980-12-20 ES ES498028A patent/ES8203355A1/es not_active Expired
- 1980-12-20 GR GR63731A patent/GR72809B/el unknown
-
1981
- 1981-11-12 US US06/320,262 patent/US4360530A/en not_active Expired - Fee Related
-
1984
- 1984-10-05 KR KR1019840006157A patent/KR850000210B1/ko not_active Expired
-
1985
- 1985-12-30 MY MY271/85A patent/MY8500271A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: F. HOFFMANN-LA ROCHE & CO. |