DE1645904B1 - 3-Hydroxy-7-chlor-1,2-dihydro-3 H-1,4-benzodiazepin-2-on-derivate - Google Patents
3-Hydroxy-7-chlor-1,2-dihydro-3 H-1,4-benzodiazepin-2-on-derivateInfo
- Publication number
- DE1645904B1 DE1645904B1 DE19621645904 DE1645904A DE1645904B1 DE 1645904 B1 DE1645904 B1 DE 1645904B1 DE 19621645904 DE19621645904 DE 19621645904 DE 1645904 A DE1645904 A DE 1645904A DE 1645904 B1 DE1645904 B1 DE 1645904B1
- Authority
- DE
- Germany
- Prior art keywords
- benzodiazepin
- dihydro
- hydroxy
- chloro
- derivatives
- 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.)
- Pending
Links
- XTYLCEPMEBVKJQ-UHFFFAOYSA-N OC1N=CC(C=C(C=C2)Cl)=C2NC1=O Chemical class OC1N=CC(C=C(C=C2)Cl)=C2NC1=O XTYLCEPMEBVKJQ-UHFFFAOYSA-N 0.000 title 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- -1 acyloxy radical Chemical class 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 7
- 230000008485 antagonism Effects 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 206010010904 Convulsion Diseases 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 230000034994 death Effects 0.000 description 4
- 231100000517 death Toxicity 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 206010003591 Ataxia Diseases 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 229960004782 chlordiazepoxide Drugs 0.000 description 2
- 230000036461 convulsion Effects 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 231100000636 lethal dose Toxicity 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229960005181 morphine Drugs 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- ADIMAYPTOBDMTL-UHFFFAOYSA-N oxazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1 ADIMAYPTOBDMTL-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- FYRWUTOZBRWYCS-UHFFFAOYSA-N (7-chloro-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl) acetate Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(OC(=O)C)N=C1C1=CC=CC=C1 FYRWUTOZBRWYCS-UHFFFAOYSA-N 0.000 description 1
- RGGLEJFUEMKQSH-UHFFFAOYSA-N 1,4-benzodiazepin-2-one Chemical compound O=C1C=NC=C2C=CC=CC2=N1 RGGLEJFUEMKQSH-UHFFFAOYSA-N 0.000 description 1
- JSUAJTLKVREZHV-UHFFFAOYSA-N 1-[4-(1-pyrrolidinyl)but-2-ynyl]pyrrolidine Chemical compound C1CCCN1CC#CCN1CCCC1 JSUAJTLKVREZHV-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- NOXIPAREWUQUGI-UHFFFAOYSA-N 3,7-dichloro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(Cl)N=C1C1=CC=CC=C1 NOXIPAREWUQUGI-UHFFFAOYSA-N 0.000 description 1
- 206010053398 Clonic convulsion Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 206010021118 Hypotonia Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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
- 206010023644 Lacrimation increased Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- 206010039424 Salivary hypersecretion Diseases 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 206010043994 Tonic convulsion Diseases 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- CYDZMDOLVUBPNL-UHFFFAOYSA-N [7-chloro-5-(2-chlorophenyl)-2-oxo-1,3-dihydro-1,4-benzodiazepin-3-yl] acetate Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(OC(=O)C)N=C1C1=CC=CC=C1Cl CYDZMDOLVUBPNL-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000002566 clonic effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 230000004317 lacrimation Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
- 229960004715 morphine sulfate Drugs 0.000 description 1
- GRVOTVYEFDAHCL-RTSZDRIGSA-N morphine sulfate pentahydrate Chemical compound O.O.O.O.O.OS(O)(=O)=O.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O GRVOTVYEFDAHCL-RTSZDRIGSA-N 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 208000026451 salivation Diseases 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/06—Catalysts
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/18—Copolymerisation of aldehydes or ketones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/18—Copolymerisation of aldehydes or ketones
- C08G2/22—Copolymerisation of aldehydes or ketones with epoxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Polyethers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13456961A | 1961-08-29 | 1961-08-29 | |
| US17717462A | 1962-03-05 | 1962-03-05 | |
| US37974064A | 1964-07-01 | 1964-07-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1645904B1 true DE1645904B1 (de) | 1970-08-06 |
Family
ID=27384605
Family Applications (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19621645904 Pending DE1645904B1 (de) | 1961-08-29 | 1962-08-17 | 3-Hydroxy-7-chlor-1,2-dihydro-3 H-1,4-benzodiazepin-2-on-derivate |
| DE1795553A Expired DE1795553C3 (de) | 1961-08-29 | 1962-08-17 | S-Acyloxy-S-phenyl-SH-l^-dihydro-1,4-benzodiazepinon-(2)-derivate. Ausscheidung aus: 1445412 |
| DE1795509A Expired DE1795509C3 (de) | 1961-08-29 | 1962-08-17 | Verfahren zur Herstellung von 3-Hydroxy- 7- ch lor-1,2-dihydro-3 H-1,4-benzodiazepin-2-on-derivaten. Ausscheidung aus: 1645904 |
| DE1645903A Expired DE1645903C3 (de) | 1961-08-29 | 1962-08-17 | Verfahren zur Herstellung von 3 Halogen-3H-1,2-dihydro-1,4-benzodiazepin-2-on-derivaten |
| DE1795556A Expired DE1795556C3 (de) | 1961-08-29 | 1962-08-17 | 3,7-Dichlor-5-phenyl-l,2-dihydro-3H-1 ^-benzodiazepin-i-on. Ausscheidung aus: 1645903 |
| DE19621445412 Pending DE1445412A1 (de) | 1961-08-29 | 1962-08-17 | Verfahren zur Herstellung von 3-Acyloxy-3H-1,2-dihydro-1,4-benzodiazepin-2-on-derivaten |
| DE19651570365 Pending DE1570365B2 (de) | 1961-08-29 | 1965-06-30 | Verfahren zur Herstellung von Copolymerisaten des Trioxans |
| DE19651795558 Pending DE1795558A1 (de) | 1961-08-29 | 1965-06-30 | Neue Copolymere aus Trioxan und oxacyclischen Comonomeren |
Family Applications After (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1795553A Expired DE1795553C3 (de) | 1961-08-29 | 1962-08-17 | S-Acyloxy-S-phenyl-SH-l^-dihydro-1,4-benzodiazepinon-(2)-derivate. Ausscheidung aus: 1445412 |
| DE1795509A Expired DE1795509C3 (de) | 1961-08-29 | 1962-08-17 | Verfahren zur Herstellung von 3-Hydroxy- 7- ch lor-1,2-dihydro-3 H-1,4-benzodiazepin-2-on-derivaten. Ausscheidung aus: 1645904 |
| DE1645903A Expired DE1645903C3 (de) | 1961-08-29 | 1962-08-17 | Verfahren zur Herstellung von 3 Halogen-3H-1,2-dihydro-1,4-benzodiazepin-2-on-derivaten |
| DE1795556A Expired DE1795556C3 (de) | 1961-08-29 | 1962-08-17 | 3,7-Dichlor-5-phenyl-l,2-dihydro-3H-1 ^-benzodiazepin-i-on. Ausscheidung aus: 1645903 |
| DE19621445412 Pending DE1445412A1 (de) | 1961-08-29 | 1962-08-17 | Verfahren zur Herstellung von 3-Acyloxy-3H-1,2-dihydro-1,4-benzodiazepin-2-on-derivaten |
| DE19651570365 Pending DE1570365B2 (de) | 1961-08-29 | 1965-06-30 | Verfahren zur Herstellung von Copolymerisaten des Trioxans |
| DE19651795558 Pending DE1795558A1 (de) | 1961-08-29 | 1965-06-30 | Neue Copolymere aus Trioxan und oxacyclischen Comonomeren |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3435005A (en, 2012) |
| BE (2) | BE666274A (en, 2012) |
| BR (1) | BR6242421D0 (en, 2012) |
| CA (1) | CA963004A (en, 2012) |
| CH (4) | CH446362A (en, 2012) |
| CY (2) | CY386A (en, 2012) |
| DE (8) | DE1645904B1 (en, 2012) |
| DK (2) | DK127600B (en, 2012) |
| FI (4) | FI46072C (en, 2012) |
| FR (1) | FR2217M (en, 2012) |
| GB (5) | GB1022645A (en, 2012) |
| IL (1) | IL23813A (en, 2012) |
| LU (1) | LU48964A1 (en, 2012) |
| MY (3) | MY6900345A (en, 2012) |
| NL (1) | NL6508496A (en, 2012) |
| SE (5) | SE335734B (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL261058A (en, 2012) * | 1960-05-19 | |||
| DE1795231C3 (de) * | 1963-05-29 | 1978-07-13 | American Home Products Corp., New York, N.Y. (V.St.A.) | Verfahren zur Herstellung von 5-Aryl-1,2-dihydro -3H-1,4-benzodiazepin-2-on-4-oxyden |
| BE788899A (fr) * | 1971-09-15 | 1973-01-02 | Crc Ricerca Chim | Procede de preparation de derives de benzodiazepine-1,4 one-2 utiles notamment comme agents tranquillisants et sedatifs |
| ES405260A1 (es) * | 1972-07-28 | 1975-07-01 | Stabilimenti Chim Farmac Riuni | Procedimiento para la preparacion de 3-hidroxi-5-aril-7- sustituidos-1, 3-dihidro-2h-1, 4-benzodiacepin-2-onas. |
| FI783743A7 (fi) * | 1977-12-14 | 1979-06-15 | Gerot Pharmazeutika | Foerfarande foer framstaellning av 3-di-n-propyl-acetoxi-benzodiazepin-2-oner |
| AT361492B (de) * | 1978-12-18 | 1981-03-10 | Gerot Pharmazeutika | Verfahren zur herstellung von neuen 3-hydroxy- 1,4-benzodiazepin-2-onen |
| US4540727A (en) * | 1982-10-29 | 1985-09-10 | Raychem Corporation | Polyamide compositions |
| IT1165588B (it) * | 1983-03-23 | 1987-04-22 | Medosan Ind Biochimi | 1,4 benzodiazepine terapeuticamente attive |
| AU2001245429A1 (en) * | 2000-03-06 | 2001-09-17 | Teva Pharmaqceutical Industries Ltd. | Process for preparing pure crystalline lorazepam |
| CN105601576A (zh) * | 2016-03-18 | 2016-05-25 | 山东新华制药股份有限公司 | 氯甲西泮的晶型及其制备方法 |
| UA119735C2 (uk) | 2018-12-20 | 2019-07-25 | Анатолій Семенович Редер | Фармацевтична сполука, спосіб її отримання та застосування як лікарського засобу |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2457224A (en) * | 1945-07-03 | 1948-12-28 | Du Pont | Preparation of polydioxolane |
| NL180786B (nl) * | 1951-08-22 | Nat Res Dev | Inrichting voor het onderzoeken van monsters. | |
| US3027352A (en) * | 1958-02-28 | 1962-03-27 | Celanese Corp | Copolymers |
| NL271273A (en, 2012) * | 1960-11-15 | |||
| NL286742A (en, 2012) * | 1961-12-14 | |||
| US3293219A (en) * | 1963-07-10 | 1966-12-20 | Tenneco Chem | Polyacetal terpolymers containing randomly recurring groups derived from a methylene-bis- |
-
0
- BE BE621819D patent/BE621819A/xx unknown
-
1962
- 1962-08-17 DE DE19621645904 patent/DE1645904B1/de active Pending
- 1962-08-17 DE DE1795553A patent/DE1795553C3/de not_active Expired
- 1962-08-17 DE DE1795509A patent/DE1795509C3/de not_active Expired
- 1962-08-17 DE DE1645903A patent/DE1645903C3/de not_active Expired
- 1962-08-17 DE DE1795556A patent/DE1795556C3/de not_active Expired
- 1962-08-17 DE DE19621445412 patent/DE1445412A1/de active Pending
- 1962-08-24 CH CH44566A patent/CH446362A/de unknown
- 1962-08-24 CH CH1012862A patent/CH417611A/de unknown
- 1962-08-24 CH CH1244367A patent/CH467790A/de unknown
- 1962-08-27 FI FI621565A patent/FI46072C/fi active
- 1962-08-27 BR BR142421/62A patent/BR6242421D0/pt unknown
- 1962-08-28 GB GB37789/65A patent/GB1022645A/en not_active Expired
- 1962-08-28 GB GB37788/65D patent/GB1022644A/en not_active Expired
- 1962-08-28 GB GB32910/62A patent/GB1022642A/en not_active Expired
- 1962-08-28 GB GB5679/65A patent/GB1022643A/en not_active Expired
- 1962-08-28 DK DK377762AA patent/DK127600B/da unknown
- 1962-08-29 SE SE16431/67A patent/SE335734B/xx unknown
- 1962-08-29 SE SE00239/70A patent/SE368575B/xx unknown
- 1962-08-29 CA CA856,978A patent/CA963004A/en not_active Expired
- 1962-08-29 SE SE9353/62A patent/SE322225B/xx unknown
- 1962-11-26 FR FR916636A patent/FR2217M/fr active Active
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1964
- 1964-07-01 US US379740A patent/US3435005A/en not_active Expired - Lifetime
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1965
- 1965-06-14 SE SE7819/65A patent/SE323080B/xx unknown
- 1965-06-23 GB GB26539/65A patent/GB1078788A/en not_active Expired
- 1965-06-25 IL IL23813A patent/IL23813A/xx unknown
- 1965-06-25 DK DK322265AA patent/DK114514B/da unknown
- 1965-06-29 CH CH911765A patent/CH451519A/fr unknown
- 1965-06-30 DE DE19651570365 patent/DE1570365B2/de active Pending
- 1965-06-30 DE DE19651795558 patent/DE1795558A1/de active Pending
- 1965-07-01 NL NL6508496A patent/NL6508496A/xx unknown
- 1965-07-01 LU LU48964D patent/LU48964A1/xx unknown
- 1965-07-01 BE BE666274D patent/BE666274A/xx unknown
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1967
- 1967-04-25 CY CY38667A patent/CY386A/xx unknown
- 1967-08-10 FI FI672159A patent/FI46849C/fi active
- 1967-08-10 FI FI672158A patent/FI46848C/fi active
- 1967-11-29 SE SE16432/67A patent/SE337033B/xx unknown
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1968
- 1968-09-30 FI FI682762A patent/FI47371C/fi active
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1969
- 1969-07-01 CY CY49869A patent/CY498A/xx unknown
- 1969-12-31 MY MY1969345A patent/MY6900345A/xx unknown
- 1969-12-31 MY MY1969102A patent/MY6900102A/xx unknown
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1970
- 1970-12-31 MY MY197021A patent/MY7000021A/xx unknown
Non-Patent Citations (1)
| Title |
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| None * |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 |