DE1695666C3 - 10,11 -Dihydro-dibenzo- eckige Klammer auf bfl -azepinderivate, ihre Herstellung und pharmazeutische Zusammensetzungen - Google Patents
10,11 -Dihydro-dibenzo- eckige Klammer auf bfl -azepinderivate, ihre Herstellung und pharmazeutische ZusammensetzungenInfo
- Publication number
- DE1695666C3 DE1695666C3 DE1695666A DER0047820A DE1695666C3 DE 1695666 C3 DE1695666 C3 DE 1695666C3 DE 1695666 A DE1695666 A DE 1695666A DE R0047820 A DER0047820 A DE R0047820A DE 1695666 C3 DE1695666 C3 DE 1695666C3
- Authority
- DE
- Germany
- Prior art keywords
- group
- ecm
- general formula
- given above
- compound
- 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.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title description 11
- 239000008194 pharmaceutical composition Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 47
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 14
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical group OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- ZSMRRZONCYIFNB-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepine Chemical class C1CC2=CC=CC=C2NC2=CC=CC=C12 ZSMRRZONCYIFNB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 129
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- 239000012153 distilled water Substances 0.000 description 37
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 34
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- -1 methyleneamino group Chemical group 0.000 description 19
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- 230000002378 acidificating effect Effects 0.000 description 10
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- 239000011734 sodium Substances 0.000 description 9
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- 238000002425 crystallisation Methods 0.000 description 7
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
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- 239000012280 lithium aluminium hydride Substances 0.000 description 4
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- 239000002904 solvent Substances 0.000 description 4
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910001023 sodium amalgam Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- AJUMGSLQADLWKL-UHFFFAOYSA-N 1h-azepine;hydrochloride Chemical compound Cl.N1C=CC=CC=C1 AJUMGSLQADLWKL-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- ZKHZWXLOSIGIGZ-UHFFFAOYSA-N 5-methoxy-11h-benzo[b][1]benzazepine Chemical compound COC1=CC2=CC=CC=C2NC2=CC=CC=C12 ZKHZWXLOSIGIGZ-UHFFFAOYSA-N 0.000 description 2
- 229910000497 Amalgam Inorganic materials 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- RBSVEQCQZAHLGE-UHFFFAOYSA-N N-(11-methyl-5,6-dihydrobenzo[b][1]benzazepin-5-yl)formamide Chemical compound CN1C2=C(CC(C3=C1C=CC=C3)NC=O)C=CC=C2 RBSVEQCQZAHLGE-UHFFFAOYSA-N 0.000 description 2
- KGHMFPFRLWYZNF-UHFFFAOYSA-N N-methyl-N-(11-methyl-5,6-dihydrobenzo[b][1]benzazepin-5-yl)formamide Chemical compound CN1C2=C(CC(C3=C1C=CC=C3)N(C)C=O)C=CC=C2 KGHMFPFRLWYZNF-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- YXVZOBVWVRFPTE-UHFFFAOYSA-N metapramine Chemical compound CNC1CC2=CC=CC=C2N(C)C2=CC=CC=C12 YXVZOBVWVRFPTE-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
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- AFRLIBIVHBVGDG-UHFFFAOYSA-N 11-ethyl-5-methoxybenzo[b][1]benzazepine Chemical compound C1=C(OC)C2=CC=CC=C2N(CC)C2=CC=CC=C21 AFRLIBIVHBVGDG-UHFFFAOYSA-N 0.000 description 1
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- IXVJKFCFNGQJTG-UHFFFAOYSA-N 3-oxopropanoyl 3-oxopropanoate Chemical compound O=CCC(=O)OC(=O)CC=O IXVJKFCFNGQJTG-UHFFFAOYSA-N 0.000 description 1
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- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
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- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
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- 230000002349 favourable effect Effects 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229960004801 imipramine Drugs 0.000 description 1
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
- 150000002485 inorganic esters Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZDYVPIFPVZTJAL-UHFFFAOYSA-N methyl-(11-methyl-5,6-dihydrobenzo[b][1]benzazepin-5-yl)cyanamide Chemical compound CN1C2=C(CC(C3=C1C=CC=C3)N(C)C#N)C=CC=C2 ZDYVPIFPVZTJAL-UHFFFAOYSA-N 0.000 description 1
- SURZCVYFPAXNGN-UHFFFAOYSA-N methyl-carbamic acid ethyl ester Chemical compound CCOC(=O)NC SURZCVYFPAXNGN-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- BCPGMBBFDXZUKD-UHFFFAOYSA-N n,11-dimethyl-5,6-dihydrobenzo[b][1]benzazepin-5-amine;hydrochloride Chemical compound Cl.CNC1CC2=CC=CC=C2N(C)C2=CC=CC=C12 BCPGMBBFDXZUKD-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 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
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings 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
- C07D223/08—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Combustion Methods Of Internal-Combustion Engines (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Securing Globes, Refractors, Reflectors Or The Like (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR91646A FR1532301A (fr) | 1967-01-18 | 1967-01-18 | Nouveaux dérivés de la dibenzazépine et leur préparation |
| FR127611A FR94320E (fr) | 1967-01-18 | 1967-11-09 | Nouveaux dérives de la dibenzazépine et leur préparation. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1695666A1 DE1695666A1 (de) | 1972-04-06 |
| DE1695666B2 DE1695666B2 (de) | 1978-09-28 |
| DE1695666C3 true DE1695666C3 (de) | 1979-05-23 |
Family
ID=26174548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1695666A Expired DE1695666C3 (de) | 1967-01-18 | 1968-01-18 | 10,11 -Dihydro-dibenzo- eckige Klammer auf bfl -azepinderivate, ihre Herstellung und pharmazeutische Zusammensetzungen |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3622565A (enExample) |
| AT (6) | AT279630B (enExample) |
| BE (1) | BE709523A (enExample) |
| CH (1) | CH482677A (enExample) |
| DE (1) | DE1695666C3 (enExample) |
| DK (2) | DK120950B (enExample) |
| ES (5) | ES349459A1 (enExample) |
| FI (1) | FI48927C (enExample) |
| FR (2) | FR1532301A (enExample) |
| GB (2) | GB1180165A (enExample) |
| IE (1) | IE31926B1 (enExample) |
| IL (1) | IL29340A (enExample) |
| LU (1) | LU55297A1 (enExample) |
| NL (1) | NL156137B (enExample) |
| NO (2) | NO125677B (enExample) |
| OA (1) | OA03401A (enExample) |
| SE (2) | SE338995B (enExample) |
| SU (1) | SU464112A3 (enExample) |
| YU (2) | YU32142B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3882235A (en) * | 1969-06-24 | 1975-05-06 | Rhone Poulenc Sa | Fungicidal compositions comprising A 10, 11 dihydrodibenzo {8 b,f{9 {0 azepine derivative |
| FR2198942B1 (enExample) * | 1972-09-12 | 1975-03-14 | Rhone Poulenc Ind | |
| FI75561C (fi) * | 1979-10-30 | 1988-07-11 | Ciba Geigy Ag | Foerfarande foer framstaellning av 5- karbamoyl-10-oxo-10,11-dihydro-5h-dibens/b,f/azepin och daertill noedvaendiga mellanprodukter. |
| US20070225217A1 (en) | 2005-11-09 | 2007-09-27 | Combinatorx, Incorporated | Methods, compositions, and kits for the treatment of medical conditions |
| KR101539797B1 (ko) | 2007-11-28 | 2015-07-27 | 넥타르 테라퓨틱스 | 올리고머-삼환계 콘쥬게이트 |
| WO2011091050A1 (en) | 2010-01-19 | 2011-07-28 | Nektar Therapeutics | Oligomer-tricyclic conjugates |
| JP6002144B2 (ja) | 2010-12-10 | 2016-10-05 | ネクター セラピューティクス | ヒドロキシル化三環化合物 |
| KR102824220B1 (ko) | 2018-09-28 | 2025-06-23 | 그리피스 유니버시티 | 병원체 활성 조절을 위한 제제 및 방법 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH457447A (de) * | 1965-07-26 | 1968-06-15 | Geigy Ag J R | Verfahren zur Herstellung von neuen Azepinderivaten |
-
1967
- 1967-01-18 FR FR91646A patent/FR1532301A/fr not_active Expired
- 1967-11-09 FR FR127611A patent/FR94320E/fr not_active Expired
-
1968
- 1968-01-09 OA OA53156A patent/OA03401A/xx unknown
- 1968-01-10 NL NL6800363.A patent/NL156137B/xx not_active IP Right Cessation
- 1968-01-16 SE SE00553/68A patent/SE338995B/xx unknown
- 1968-01-16 FI FI680114A patent/FI48927C/fi active
- 1968-01-16 SE SE04482/70A patent/SE350971B/xx unknown
- 1968-01-16 DK DK15068AA patent/DK120950B/da not_active IP Right Cessation
- 1968-01-17 US US698436A patent/US3622565A/en not_active Expired - Lifetime
- 1968-01-17 IE IE57/68A patent/IE31926B1/xx unknown
- 1968-01-17 NO NO0200/68A patent/NO125677B/no unknown
- 1968-01-17 BE BE709523A patent/BE709523A/fr unknown
- 1968-01-17 IL IL29340A patent/IL29340A/en unknown
- 1968-01-17 LU LU55297D patent/LU55297A1/xx unknown
- 1968-01-18 AT AT03859/69A patent/AT279630B/de not_active IP Right Cessation
- 1968-01-18 SU SU1313323A patent/SU464112A3/ru active
- 1968-01-18 AT AT386169A patent/AT279632B/de not_active IP Right Cessation
- 1968-01-18 GB GB23183/69A patent/GB1180165A/en not_active Expired
- 1968-01-18 CH CH76368A patent/CH482677A/fr not_active IP Right Cessation
- 1968-01-18 AT AT53668A patent/AT279619B/de not_active IP Right Cessation
- 1968-01-18 AT AT03858/69A patent/AT281842B/de not_active IP Right Cessation
- 1968-01-18 ES ES349459A patent/ES349459A1/es not_active Expired
- 1968-01-18 DE DE1695666A patent/DE1695666C3/de not_active Expired
- 1968-01-18 AT AT385769A patent/AT279629B/de not_active IP Right Cessation
- 1968-01-18 GB GB2858/68A patent/GB1180164A/en not_active Expired
- 1968-01-18 AT AT03860/69A patent/AT279631B/de not_active IP Right Cessation
- 1968-01-18 YU YU0121/68A patent/YU32142B/xx unknown
- 1968-05-30 ES ES354502A patent/ES354502A1/es not_active Expired
- 1968-05-30 ES ES354500A patent/ES354500A1/es not_active Expired
- 1968-05-30 ES ES354501A patent/ES354501A1/es not_active Expired
- 1968-05-30 ES ES354499A patent/ES354499A1/es not_active Expired
-
1969
- 1969-01-14 DK DK19669AA patent/DK118135B/da not_active IP Right Cessation
-
1971
- 1971-11-05 NO NO4096/71*[A patent/NO126527B/no unknown
-
1972
- 1972-10-30 YU YU2692/72A patent/YU33110B/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |