DE1670772C3 - 4H-3,1-Benzoxazin-Derivate, deren Salze und pharmazeutische Präparate - Google Patents
4H-3,1-Benzoxazin-Derivate, deren Salze und pharmazeutische PräparateInfo
- Publication number
- DE1670772C3 DE1670772C3 DE1670772A DEF0050751A DE1670772C3 DE 1670772 C3 DE1670772 C3 DE 1670772C3 DE 1670772 A DE1670772 A DE 1670772A DE F0050751 A DEF0050751 A DE F0050751A DE 1670772 C3 DE1670772 C3 DE 1670772C3
- Authority
- DE
- Germany
- Prior art keywords
- chloro
- benzoxazine
- methyl
- phenyl
- general formula
- 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
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- 150000003839 salts Chemical class 0.000 title description 10
- 239000000825 pharmaceutical preparation Substances 0.000 title description 2
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- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- GOLCXWYRSKYTSP-UHFFFAOYSA-N arsenic trioxide Inorganic materials O1[As]2O[As]1O2 GOLCXWYRSKYTSP-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000005130 benzoxazines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical class NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001912 cyanamides Chemical class 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
- 229960002456 hexobarbital Drugs 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- UGVPKMAWLOMPRS-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].CC[CH2-] UGVPKMAWLOMPRS-UHFFFAOYSA-M 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
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- IGHVUURTQGBABT-UHFFFAOYSA-N methyl 2-amino-5-chlorobenzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1N IGHVUURTQGBABT-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 230000004973 motor coordination Effects 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000011356 non-aqueous organic solvent Substances 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229960005152 pentetrazol Drugs 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- KKKDGYXNGYJJRX-UHFFFAOYSA-M silver nitrite Chemical compound [Ag+].[O-]N=O KKKDGYXNGYJJRX-UHFFFAOYSA-M 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/18—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Load-Bearing And Curtain Walls (AREA)
Priority Applications (29)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1670772A DE1670772C3 (de) | 1966-11-24 | 1966-11-24 | 4H-3,1-Benzoxazin-Derivate, deren Salze und pharmazeutische Präparate |
| IL28962A IL28962A (en) | 1966-11-24 | 1967-11-17 | 3,1-benzoxazine derivatives and process for their manufacture |
| NL6715652.A NL156402B (nl) | 1966-11-24 | 1967-11-17 | Werkwijze voor het bereiden van benzoxazinederivaten, werkwijze voor het bereiden van deze verbindingen bevattende farmaceutica, alsmede aldus verkregen gevormde geneesmiddelen. |
| CS556272*1A CS154239B2 (https=) | 1966-11-24 | 1967-11-20 | |
| CS821567A CS154238B2 (https=) | 1966-11-24 | 1967-11-20 | |
| CS556472*1A CS154241B2 (https=) | 1966-11-24 | 1967-11-20 | |
| GB52643/67A GB1197479A (en) | 1966-11-24 | 1967-11-20 | 3,1-Benzoxazine Derivatives and Process for their Manufacture |
| CS556372*1A CS154240B2 (https=) | 1966-11-24 | 1967-11-20 | |
| CS793372*1A CS154242B2 (https=) | 1966-11-24 | 1967-11-20 | |
| ES347430A ES347430A1 (es) | 1966-11-24 | 1967-11-21 | Procedimiento para la obtencion de derivados de benzoxazi- na. |
| YU2271/67A YU32857B (en) | 1966-11-24 | 1967-11-21 | Postopek za pripravo novih derivatov benzoksazina |
| CH291470A CH532604A (de) | 1966-11-24 | 1967-11-22 | Verfahren zur Herstellung von 3,1-Benzoxazin-Derivaten |
| AT1136668A AT278024B (de) | 1966-11-24 | 1967-11-22 | Verfahren zur Herstellung von neuen 3,1-Benzoxazin-Derivaten und ihren Salzen |
| CH1083571A CH534174A (de) | 1966-11-24 | 1967-11-22 | Verfahren zur Herstellung von 3,1-Benzoxazin-Derivaten |
| AT1055167A AT276412B (de) | 1966-11-24 | 1967-11-22 | Verfahren zur Herstellung von neuen 3,1-Benzoxazin-Derivaten und ihren Salzen |
| CH291370A CH502366A (de) | 1966-11-24 | 1967-11-22 | Verfahren zur Herstellung von 3,1-Benzoxazin-Derivaten |
| CH291270A CH532603A (de) | 1966-11-24 | 1967-11-22 | Verfahren zur Herstellung von 3,1-Benzoxazin-Derivaten |
| CH1635167A CH522671A (de) | 1966-11-24 | 1967-11-22 | Verfahren zur Herstellung von 3,1-Benzoxazin-Derivaten |
| AT1136868A AT278026B (de) | 1966-11-24 | 1967-11-22 | Verfahren zur Herstellung von neuen 3,1-Benzoxazin-Derivaten und ihren Salzen |
| AT1136768A AT278025B (de) | 1966-11-24 | 1967-11-22 | Verfahren zur Herstellung von neuen 3,1-Benzoxazin-Derivaten und ihren Salzen |
| SE16017/67A SE329620B (https=) | 1966-11-24 | 1967-11-22 | |
| NO170669A NO119743B (https=) | 1966-11-24 | 1967-11-23 | |
| DK587767A DK131905C (da) | 1966-11-24 | 1967-11-23 | Analogifremgangsmade til fremstilling af 3,1-benzoxazinderivater og syreadditionssalte deraf |
| BE707013D BE707013A (https=) | 1966-11-24 | 1967-11-24 | |
| FI673169A FI48595C (fi) | 1966-11-24 | 1967-11-24 | Menetelmä spykotrooppisesti vaikuttavien 4-substituoitujen 2-amino-4H- 3,1-bentsoksatsiinijohdannaisten valmistamiseksi. |
| FR1571287D FR1571287A (https=) | 1966-11-24 | 1967-11-24 | |
| FR141043A FR7358M (https=) | 1966-11-24 | 1968-02-23 | |
| ES366801A ES366801A1 (es) | 1966-11-24 | 1969-05-05 | Procedimiento para la obtencion de preparados farmaceuti- cos. |
| US00151599A US3725404A (en) | 1966-11-24 | 1971-06-09 | 2-amino-4,4-di-substituted-4h-3,1-benzoxazines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1670772A DE1670772C3 (de) | 1966-11-24 | 1966-11-24 | 4H-3,1-Benzoxazin-Derivate, deren Salze und pharmazeutische Präparate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1670772A1 DE1670772A1 (de) | 1970-07-16 |
| DE1670772B2 DE1670772B2 (de) | 1977-08-25 |
| DE1670772C3 true DE1670772C3 (de) | 1978-04-20 |
Family
ID=7104042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1670772A Expired DE1670772C3 (de) | 1966-11-24 | 1966-11-24 | 4H-3,1-Benzoxazin-Derivate, deren Salze und pharmazeutische Präparate |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3725404A (https=) |
| AT (4) | AT278026B (https=) |
| BE (1) | BE707013A (https=) |
| CH (2) | CH522671A (https=) |
| CS (5) | CS154239B2 (https=) |
| DE (1) | DE1670772C3 (https=) |
| DK (1) | DK131905C (https=) |
| ES (2) | ES347430A1 (https=) |
| FI (1) | FI48595C (https=) |
| FR (2) | FR1571287A (https=) |
| GB (1) | GB1197479A (https=) |
| IL (1) | IL28962A (https=) |
| NL (1) | NL156402B (https=) |
| NO (1) | NO119743B (https=) |
| SE (1) | SE329620B (https=) |
| YU (1) | YU32857B (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670772C3 (de) * | 1966-11-24 | 1978-04-20 | Hoechst Ag, 6000 Frankfurt | 4H-3,1-Benzoxazin-Derivate, deren Salze und pharmazeutische Präparate |
| US4596801A (en) * | 1983-03-24 | 1986-06-24 | Chugai Seiyaku Kabushiki Kaisha | 4H-3,1-benzoxazine derivatives, process for producing the same and agricultural or horticultural fungicide containing the same |
| FR2888748B1 (fr) | 2005-07-19 | 2007-10-12 | Biocodex | Composes neuroprotecteurs et compositions pharmaceutiques les comprenant |
| FR2888749B1 (fr) | 2005-07-19 | 2007-10-12 | Biocodex | Composition pharmaceutique destinee a la prevention ou au traitement des oedemes cerebraux |
| US8110569B2 (en) * | 2006-03-20 | 2012-02-07 | The Regents Of The University Of California | Enantiomerically pure S-etifoxine, pharmaceutical compositions thereof and methods of their use |
| US20080039453A1 (en) * | 2006-03-20 | 2008-02-14 | David Putman | Enantiomerically pure R-etifoxine, pharmaceutical compositions thereof and methods of their use |
| FR2930891B1 (fr) * | 2008-05-06 | 2010-09-24 | Biocodex | Composes anti-amnesiants et compositions pharmaceutiques les comprenant |
| FR2937552B1 (fr) | 2008-10-27 | 2011-05-06 | Biocodex | Composition pharmaceutique destinee a la prevention ou au traitement du syndrome de sevrage alcoolique |
| US20120071471A1 (en) * | 2009-03-13 | 2012-03-22 | Neurosearch A/S | Novel benzoxazinone derivatives useful for the treatment of cns disorders |
| FR2972192A1 (fr) * | 2011-03-04 | 2012-09-07 | Biocodex | Composition pharmaceutique destinee a la prevention ou au traitement des cancers |
| FR3016881B1 (fr) | 2014-01-29 | 2016-03-04 | Biocodex | Traitement des degenerescences et des lesions photo-induites de la retine |
| EP3347006B1 (en) | 2015-03-20 | 2022-07-27 | GABA Therapeutics Inc. | Deuterated analogs of etifoxine, their derivatives and uses therof |
| CN108884025A (zh) * | 2016-03-31 | 2018-11-23 | 陶氏环球技术有限责任公司 | 双碳二亚胺和聚碳二亚胺及其制备方法 |
| FR3051114B1 (fr) | 2016-05-11 | 2019-09-27 | Biocodex | Composes pour le traitement de la maladie d'alzheimer |
| US10420773B2 (en) | 2017-09-26 | 2019-09-24 | Ovid Therapeutics Inc. | Methods of treating developmental disorders and/or seizure disorders with etifoxine |
| CN117586198B (zh) * | 2023-11-24 | 2024-10-25 | 南开大学 | 溴苯并恶嗪类化合物的合成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1545820A1 (de) * | 1965-06-03 | 1969-12-11 | Hoechst Ag | Verfahren zur Herstellung von 3,1-Benzothiazin-Derivaten |
| DE1670772C3 (de) * | 1966-11-24 | 1978-04-20 | Hoechst Ag, 6000 Frankfurt | 4H-3,1-Benzoxazin-Derivate, deren Salze und pharmazeutische Präparate |
-
1966
- 1966-11-24 DE DE1670772A patent/DE1670772C3/de not_active Expired
-
1967
- 1967-11-17 NL NL6715652.A patent/NL156402B/xx not_active IP Right Cessation
- 1967-11-17 IL IL28962A patent/IL28962A/en unknown
- 1967-11-20 GB GB52643/67A patent/GB1197479A/en not_active Expired
- 1967-11-20 CS CS556272*1A patent/CS154239B2/cs unknown
- 1967-11-20 CS CS821567A patent/CS154238B2/cs unknown
- 1967-11-20 CS CS793372*1A patent/CS154242B2/cs unknown
- 1967-11-20 CS CS556472*1A patent/CS154241B2/cs unknown
- 1967-11-20 CS CS556372*1A patent/CS154240B2/cs unknown
- 1967-11-21 ES ES347430A patent/ES347430A1/es not_active Expired
- 1967-11-21 YU YU2271/67A patent/YU32857B/xx unknown
- 1967-11-22 SE SE16017/67A patent/SE329620B/xx unknown
- 1967-11-22 AT AT1136868A patent/AT278026B/de not_active IP Right Cessation
- 1967-11-22 CH CH1635167A patent/CH522671A/de not_active IP Right Cessation
- 1967-11-22 AT AT1055167A patent/AT276412B/de active
- 1967-11-22 CH CH1083571A patent/CH534174A/de not_active IP Right Cessation
- 1967-11-22 AT AT1136668A patent/AT278024B/de not_active IP Right Cessation
- 1967-11-22 AT AT1136768A patent/AT278025B/de not_active IP Right Cessation
- 1967-11-23 DK DK587767A patent/DK131905C/da not_active IP Right Cessation
- 1967-11-23 NO NO170669A patent/NO119743B/no unknown
- 1967-11-24 FR FR1571287D patent/FR1571287A/fr not_active Expired
- 1967-11-24 FI FI673169A patent/FI48595C/fi active
- 1967-11-24 BE BE707013D patent/BE707013A/xx not_active IP Right Cessation
-
1968
- 1968-02-23 FR FR141043A patent/FR7358M/fr not_active Expired
-
1969
- 1969-05-05 ES ES366801A patent/ES366801A1/es not_active Expired
-
1971
- 1971-06-09 US US00151599A patent/US3725404A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AT278024B (de) | 1970-01-26 |
| ES366801A1 (es) | 1971-07-16 |
| FI48595C (fi) | 1974-11-11 |
| IL28962A (en) | 1972-05-30 |
| CS154242B2 (https=) | 1974-03-29 |
| AT276412B (de) | 1969-11-25 |
| CS154241B2 (https=) | 1974-03-29 |
| DK131905C (da) | 1976-02-23 |
| AT278025B (de) | 1970-01-26 |
| US3725404A (en) | 1973-04-03 |
| FR1571287A (https=) | 1969-06-20 |
| YU227167A (en) | 1974-10-31 |
| DE1670772B2 (de) | 1977-08-25 |
| DE1670772A1 (de) | 1970-07-16 |
| CS154239B2 (https=) | 1974-03-29 |
| BE707013A (https=) | 1968-05-24 |
| FR7358M (https=) | 1969-10-20 |
| CH534174A (de) | 1973-02-28 |
| GB1197479A (en) | 1970-07-08 |
| CS154240B2 (https=) | 1974-03-29 |
| FI48595B (https=) | 1974-07-31 |
| NL156402B (nl) | 1978-04-17 |
| AT278026B (de) | 1970-01-26 |
| SE329620B (https=) | 1970-10-19 |
| YU32857B (en) | 1975-10-31 |
| NO119743B (https=) | 1970-06-29 |
| DK131905B (da) | 1975-09-22 |
| ES347430A1 (es) | 1969-11-01 |
| CS154238B2 (https=) | 1974-03-29 |
| CH522671A (de) | 1972-06-30 |
| NL6715652A (https=) | 1968-05-27 |
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