FI63229C - Foerfarande foer framstaellning av analgetiskt verkande racemiskt eller diastereomera och optiskt aktiva 2-tetrahydrofurfuryl-5,9 beta-dimetyl-6,7-bensomorfaner och deras syraadditionssalter - Google Patents
Foerfarande foer framstaellning av analgetiskt verkande racemiskt eller diastereomera och optiskt aktiva 2-tetrahydrofurfuryl-5,9 beta-dimetyl-6,7-bensomorfaner och deras syraadditionssalter Download PDFInfo
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- FI63229C FI63229C FI752211A FI752211A FI63229C FI 63229 C FI63229 C FI 63229C FI 752211 A FI752211 A FI 752211A FI 752211 A FI752211 A FI 752211A FI 63229 C FI63229 C FI 63229C
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- FI
- Finland
- Prior art keywords
- formula
- compounds
- dimethyl
- tetrahydrofurfuryl
- group
- Prior art date
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- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- GRTOGORTSDXSFK-XJTZBENFSA-N ajmalicine Chemical compound C1=CC=C2C(CCN3C[C@@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 GRTOGORTSDXSFK-XJTZBENFSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 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
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000019788 craving Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- NSPJNIDYTSSIIY-UHFFFAOYSA-N methoxy(methoxymethoxy)methane Chemical class COCOCOC NSPJNIDYTSSIIY-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- XRKQMIFKHDXFNQ-UHFFFAOYSA-N n-cyclohexyl-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)C1CCCCC1 XRKQMIFKHDXFNQ-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- DVCFNCQPOANJGU-UHFFFAOYSA-N oxolane-2-carbonyl chloride Chemical compound ClC(=O)C1CCCO1 DVCFNCQPOANJGU-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000008379 phenol ethers Chemical group 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940107700 pyruvic acid Drugs 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
- 230000035484 reaction time Effects 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 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
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2437610 | 1974-08-05 | ||
| DE2437610A DE2437610A1 (de) | 1974-08-05 | 1974-08-05 | Neue 5,9-beta-disubstituierte 2-tetrahydrofurfuryl-6,7-benzomorphane, deren saeureadditionssalze, ihre verwendung als arzneimittel und verfahren zu deren herstellung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI752211A7 FI752211A7 (is") | 1976-02-06 |
| FI63229B FI63229B (fi) | 1983-01-31 |
| FI63229C true FI63229C (fi) | 1983-05-10 |
Family
ID=5922448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI752211A FI63229C (fi) | 1974-08-05 | 1975-08-04 | Foerfarande foer framstaellning av analgetiskt verkande racemiskt eller diastereomera och optiskt aktiva 2-tetrahydrofurfuryl-5,9 beta-dimetyl-6,7-bensomorfaner och deras syraadditionssalter |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US3982005A (is") |
| JP (1) | JPS60358B2 (is") |
| AT (1) | AT348140B (is") |
| BE (1) | BE832099R (is") |
| BG (3) | BG25088A3 (is") |
| CA (1) | CA1049008A (is") |
| CH (7) | CH613963A5 (is") |
| CS (1) | CS189717B2 (is") |
| DD (1) | DD122685A5 (is") |
| DE (1) | DE2437610A1 (is") |
| DK (1) | DK138992C (is") |
| ES (6) | ES452766A1 (is") |
| FI (1) | FI63229C (is") |
| FR (1) | FR2320096A2 (is") |
| GB (1) | GB1513950A (is") |
| HU (1) | HU177952B (is") |
| IE (1) | IE42216B1 (is") |
| IL (1) | IL47860A (is") |
| LU (1) | LU73138A1 (is") |
| NL (1) | NL7509249A (is") |
| NO (1) | NO143460C (is") |
| PH (1) | PH13687A (is") |
| PL (3) | PL99816B1 (is") |
| RO (3) | RO67390A (is") |
| SE (1) | SE425392B (is") |
| SU (3) | SU591147A3 (is") |
| ZA (1) | ZA754997B (is") |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4087532A (en) * | 1974-03-09 | 1978-05-02 | Boehringer Ingelheim Gmbh | Analgesically useful 2-tetrahydrofurfuryl-5-lower alkyl-2-oxy-6,7-benzomorphans and salts thereof |
| GB1575009A (en) * | 1976-06-21 | 1980-09-17 | Acf Chemiefarma Nv | 6,7-benzomorphan derivatives |
| DE2716687A1 (de) * | 1977-04-15 | 1978-10-19 | Boehringer Sohn Ingelheim | 2'-hydroxy-2-(5-isoxazolylmethyl)-6,7benzomorphane, deren saeureadditionssalze und diese enthaltende arzneimittel |
| NL7804509A (nl) * | 1978-04-26 | 1979-10-30 | Acf Chemiefarma Nv | Nieuwe 6,7-benzomorfanderivaten en zuuradditiezouten daarvan. |
| DE2828039A1 (de) * | 1978-06-26 | 1980-01-10 | Boehringer Sohn Ingelheim | 2-(2-alkoxyethyl)-2'-hydroxy-6,7-benzomorphane deren saeureadditionssalze diese enthaltende arzneimittel und verfahren zu deren herstellung |
| JPS5636521A (en) * | 1979-08-31 | 1981-04-09 | Shin Etsu Chem Co Ltd | Production of alkenyloxy group-containing organopolysiloxane |
| TW200911796A (en) | 2007-07-26 | 2009-03-16 | Vitae Pharmaceuticals Inc | Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1 |
| EP2220048B1 (en) | 2007-11-16 | 2017-01-25 | Boehringer Ingelheim International GmbH | Aryl- and heteroarylcarbonyl derivatives of benzomorphanes and related scaffolds, medicaments containing such compounds and their use |
| CA2708303A1 (en) | 2007-12-11 | 2009-06-18 | Vitae Pharmaceuticals, Inc. | Cyclic urea inhibitors of 11.beta.-hydroxysteroid dehydrogenase 1 |
| TW200934490A (en) | 2008-01-07 | 2009-08-16 | Vitae Pharmaceuticals Inc | Lactam inhibitors of 11 &abgr;-hydroxysteroid dehydrogenase 1 |
| WO2009094169A1 (en) | 2008-01-24 | 2009-07-30 | Vitae Pharmaceuticals, Inc. | Cyclic carbazate and semicarbazide inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| EP2254872A2 (en) | 2008-02-15 | 2010-12-01 | Vitae Pharmaceuticals, Inc. | Cycloalkyl lactame derivatives as inhibitors of 11-beta-hydroxysteroid dehydrogenase 1 |
| CA2723034A1 (en) | 2008-05-01 | 2009-11-05 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| CL2009001059A1 (es) | 2008-05-01 | 2010-11-12 | Boehringer Ingelheim Int | Compuestos derivados de 1,3-oxazin-2-ona-3,6 sustituidos, inhibidores de la actividad de la 11-beta-hidroxiesteroide deshidrogenasa i; composicion farmaceutica que los comprende; utiles en el tratamiento de enfermedades tales como diabetes mellitus, entre otras. |
| US8569292B2 (en) | 2008-05-01 | 2013-10-29 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1 |
| JP5711115B2 (ja) | 2008-05-13 | 2015-04-30 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ベンゾモルファン及び関連骨格のアリサイクリックカルボン酸誘導体、そのような化合物を含有する医薬及びその使用 |
| ES2432150T3 (es) | 2008-07-25 | 2013-12-02 | Boehringer Ingelheim International Gmbh | Inhibidores cíclicos de la 11 beta-hidroxiesteroide deshidrogenasa 1 |
| US8846668B2 (en) | 2008-07-25 | 2014-09-30 | Vitae Pharmaceuticals, Inc. | Inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| US8680093B2 (en) | 2009-04-30 | 2014-03-25 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| WO2011011123A1 (en) | 2009-06-11 | 2011-01-27 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 based on the 1,3 -oxazinan- 2 -one structure |
| AR078887A1 (es) | 2009-11-06 | 2011-12-07 | Boehringer Ingelheim Int | Derivados arilo y heteroarilcarbonilo de hexahidroindenopiridina y octahidrobenzoquinolina y composiciones farmaceuticas que los contienen. |
| WO2011159760A1 (en) | 2010-06-16 | 2011-12-22 | Vitae Pharmaceuticals, Inc. | Substituted 5-,6- and 7-membered heterocycles, medicaments containing such compounds, and their use |
| TWI537258B (zh) | 2010-11-05 | 2016-06-11 | 百靈佳殷格翰國際股份有限公司 | 六氫茚并吡啶及八氫苯并喹啉之芳基－及雜環芳基羰基衍生物 |
| JP2014524438A (ja) | 2011-08-17 | 2014-09-22 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | インデノピリジン誘導体 |
| JP7574861B2 (ja) | 2020-11-26 | 2024-10-29 | 信越化学工業株式会社 | 室温硬化性オルガノポリシロキサン組成物及び物品並びに加水分解性オルガノシラン化合物及びその製造方法 |
| CN117881724A (zh) | 2021-09-03 | 2024-04-12 | 信越化学工业株式会社 | 有机聚硅氧烷化合物、室温固化性有机聚硅氧烷组合物和物品 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE582575A (is") * | 1958-09-22 | |||
| US3700734A (en) * | 1969-01-23 | 1972-10-24 | Merck & Co Inc | 2{40 -hydroxy-2,3,5-trimethyl-6,7-benzomorphan |
| DE2105743C3 (de) * | 1971-02-08 | 1979-11-29 | Boehringer Sohn Ingelheim | 2-(Furylmethyl)- a -5,9-dialkyl -6,7benzomorphane, Verfahren zu ihrer Herstellung und deren Verwendung |
| CS166803B2 (is") * | 1971-02-08 | 1976-03-29 | Boehringer Sohn Ingelheim | |
| DE2200596A1 (de) * | 1972-01-07 | 1973-07-12 | Boehringer Sohn Ingelheim | N-(furyl-methyl)-2'-hydroxy-5-phenyl6,7-benzomorphane, deren saeureadditionssalze sowie verfahren zu deren herstellung |
| DE2217420C3 (de) * | 1972-04-12 | 1981-03-12 | C.H. Boehringer Sohn, 6507 Ingelheim | N-Thienylmethyl-Heterocyclen, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zubereitungen |
| DE2229695A1 (de) * | 1972-06-19 | 1974-01-31 | Boehringer Sohn Ingelheim | 2-(heteroaryl-methyl)-5,9 beta-dialkyl6,7-benzomorphane, deren saeureadditionssalze sowie verfahren zu deren herstellung |
-
1974
- 1974-08-05 DE DE2437610A patent/DE2437610A1/de not_active Ceased
-
1975
- 1975-07-08 AT AT523775A patent/AT348140B/de not_active IP Right Cessation
- 1975-07-25 SU SU752162235A patent/SU591147A3/ru active
- 1975-07-30 RO RO7583017A patent/RO67390A/ro unknown
- 1975-07-30 JP JP50092995A patent/JPS60358B2/ja not_active Expired
- 1975-07-30 US US05/600,374 patent/US3982005A/en not_active Expired - Lifetime
- 1975-07-31 CH CH1002475A patent/CH613963A5/xx not_active IP Right Cessation
- 1975-07-31 RO RO7593232A patent/RO72735A/ro unknown
- 1975-07-31 RO RO7593231A patent/RO72736A/ro unknown
- 1975-08-01 CA CA75232728A patent/CA1049008A/en not_active Expired
- 1975-08-02 BG BG030726A patent/BG25088A3/xx unknown
- 1975-08-02 BG BG031842A patent/BG25089A3/xx unknown
- 1975-08-02 BG BG031843A patent/BG25090A3/xx unknown
- 1975-08-04 LU LU73138A patent/LU73138A1/xx unknown
- 1975-08-04 GB GB32576/75A patent/GB1513950A/en not_active Expired
- 1975-08-04 DD DD187666A patent/DD122685A5/xx unknown
- 1975-08-04 NO NO752731A patent/NO143460C/no unknown
- 1975-08-04 PL PL1975190659A patent/PL99816B1/pl unknown
- 1975-08-04 PH PH17443A patent/PH13687A/en unknown
- 1975-08-04 NL NL7509249A patent/NL7509249A/xx not_active Application Discontinuation
- 1975-08-04 HU HU75BO1566A patent/HU177952B/hu unknown
- 1975-08-04 FI FI752211A patent/FI63229C/fi not_active IP Right Cessation
- 1975-08-04 DK DK352875A patent/DK138992C/da active
- 1975-08-04 ZA ZA754997A patent/ZA754997B/xx unknown
- 1975-08-04 CS CS755425A patent/CS189717B2/cs unknown
- 1975-08-04 IL IL47860A patent/IL47860A/xx unknown
- 1975-08-04 BE BE158924A patent/BE832099R/xx not_active IP Right Cessation
- 1975-08-04 SE SE7508789A patent/SE425392B/xx not_active IP Right Cessation
- 1975-08-04 PL PL1975190658A patent/PL99819B1/pl unknown
- 1975-08-04 PL PL1975182528A patent/PL99838B1/pl unknown
- 1975-08-05 FR FR7524380A patent/FR2320096A2/fr active Granted
- 1975-08-05 IE IE1738/75A patent/IE42216B1/en unknown
-
1976
- 1976-04-16 SU SU762346108A patent/SU587859A3/ru active
- 1976-04-16 SU SU762346107A patent/SU587858A3/ru active
- 1976-10-27 ES ES452766A patent/ES452766A1/es not_active Expired
- 1976-10-27 ES ES452767A patent/ES452767A1/es not_active Expired
- 1976-10-27 ES ES452765A patent/ES452765A1/es not_active Expired
- 1976-10-27 ES ES452768A patent/ES452768A1/es not_active Expired
- 1976-10-27 ES ES452764A patent/ES452764A1/es not_active Expired
- 1976-10-27 ES ES452763A patent/ES452763A1/es not_active Expired
-
1979
- 1979-04-26 CH CH393479A patent/CH615679A5/de not_active IP Right Cessation
- 1979-04-26 CH CH393279A patent/CH615678A5/de not_active IP Right Cessation
- 1979-04-26 CH CH393379A patent/CH616420A5/de not_active IP Right Cessation
- 1979-04-26 CH CH393679A patent/CH615680A5/de not_active IP Right Cessation
- 1979-04-26 CH CH393579A patent/CH616421A5/de not_active IP Right Cessation
- 1979-04-26 CH CH393179A patent/CH615677A5/de not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: C.H. BOEHRINGER SOHN |