CN103228642B - (4a-R,9a-S)-1-(1H-苯并咪唑-5-羰基)-2,3,4,4a,9,9a-六氢-1H-茚并[2,1-b]吡啶-6-甲腈盐酸盐的晶型及其作为HSD1抑制剂的用途 - Google Patents
(4a-R,9a-S)-1-(1H-苯并咪唑-5-羰基)-2,3,4,4a,9,9a-六氢-1H-茚并[2,1-b]吡啶-6-甲腈盐酸盐的晶型及其作为HSD1抑制剂的用途 Download PDFInfo
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- CN103228642B CN103228642B CN201180053044.5A CN201180053044A CN103228642B CN 103228642 B CN103228642 B CN 103228642B CN 201180053044 A CN201180053044 A CN 201180053044A CN 103228642 B CN103228642 B CN 103228642B
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- Prior art keywords
- compound
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- alkyl
- benzo
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- YWYAUYAEQBYZFN-UHFFFAOYSA-N C(CC1)CN1C1=Cc2ccccc2CC1 Chemical compound C(CC1)CN1C1=Cc2ccccc2CC1 YWYAUYAEQBYZFN-UHFFFAOYSA-N 0.000 description 1
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- LBAQQTSCGXLKTE-UHFFFAOYSA-N CC(C)(C)OC(N(CCC1)C(CCc2ccc3)C1c2c3Oc1ccc(C)nn1)=O Chemical compound CC(C)(C)OC(N(CCC1)C(CCc2ccc3)C1c2c3Oc1ccc(C)nn1)=O LBAQQTSCGXLKTE-UHFFFAOYSA-N 0.000 description 1
- ZTXUNQRBUQZFKB-CABCVRRESA-N CC(C)(C)OC(N(CCC1)[C@@H](Cc2c3)[C@H]1c2ccc3N)=O Chemical compound CC(C)(C)OC(N(CCC1)[C@@H](Cc2c3)[C@H]1c2ccc3N)=O ZTXUNQRBUQZFKB-CABCVRRESA-N 0.000 description 1
- DMRVUOGOKZNPAD-SJORKVTESA-N CC(C)(C)OC(N(CCC1)[C@@H](Cc2c3)[C@H]1c2ccc3NC(C)=O)=O Chemical compound CC(C)(C)OC(N(CCC1)[C@@H](Cc2c3)[C@H]1c2ccc3NC(C)=O)=O DMRVUOGOKZNPAD-SJORKVTESA-N 0.000 description 1
- CWXUCOIJSLPOCZ-UHFFFAOYSA-N CC(C)(CC(C1)=O)c2c1cccc2 Chemical compound CC(C)(CC(C1)=O)c2c1cccc2 CWXUCOIJSLPOCZ-UHFFFAOYSA-N 0.000 description 1
- PZPNOBHGUGMXTR-UHFFFAOYSA-N CC(C)(CC1NCCCC11)c2c1cccc2 Chemical compound CC(C)(CC1NCCCC11)c2c1cccc2 PZPNOBHGUGMXTR-UHFFFAOYSA-N 0.000 description 1
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- 0 CC(C)*(C=N)=C Chemical compound CC(C)*(C=N)=C 0.000 description 1
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- YARVCOSUDNVNIX-UHFFFAOYSA-N CC1(C)c(cccc2)c2-c2cccnc2C1 Chemical compound CC1(C)c(cccc2)c2-c2cccnc2C1 YARVCOSUDNVNIX-UHFFFAOYSA-N 0.000 description 1
- KHTSPUXHOPPNLZ-UHFFFAOYSA-N CCC12c3ccccc3CCC1=NCC=C2 Chemical compound CCC12c3ccccc3CCC1=NCC=C2 KHTSPUXHOPPNLZ-UHFFFAOYSA-N 0.000 description 1
- KRONCEYPFSEEDT-UHFFFAOYSA-N CCC1c2cc(C)ccc2CCC1=O Chemical compound CCC1c2cc(C)ccc2CCC1=O KRONCEYPFSEEDT-UHFFFAOYSA-N 0.000 description 1
- DMFFSBZFOUFDQX-JFGZAKSSSA-N CC[C@@]1(CCC2)c3ccccc3CCC1N2C(c(cc1)cc2c1[nH]cn2)=O Chemical compound CC[C@@]1(CCC2)c3ccccc3CCC1N2C(c(cc1)cc2c1[nH]cn2)=O DMFFSBZFOUFDQX-JFGZAKSSSA-N 0.000 description 1
- XOTGUYBYWPDVDS-VTBWFHPJSA-N CN(c(ccc(C(N(CCC1)C2[C@H]1c1ccccc1C2)=O)c1)c1N1)C1=O Chemical compound CN(c(ccc(C(N(CCC1)C2[C@H]1c1ccccc1C2)=O)c1)c1N1)C1=O XOTGUYBYWPDVDS-VTBWFHPJSA-N 0.000 description 1
- LISKEUTZSMPTKL-UZLBHIALSA-N COC(c1cc([C@@H](CCC2)[C@H](C3)N2C(c2ccc4[nH]cnc4c2)=O)c3cc1)=O Chemical compound COC(c1cc([C@@H](CCC2)[C@H](C3)N2C(c2ccc4[nH]cnc4c2)=O)c3cc1)=O LISKEUTZSMPTKL-UZLBHIALSA-N 0.000 description 1
- YKJMSVPGIQUKAE-UHFFFAOYSA-N COc(cc1)c(CCC(C2CCC3)N3C(c3ccccc3)=O)c2c1OC Chemical compound COc(cc1)c(CCC(C2CCC3)N3C(c3ccccc3)=O)c2c1OC YKJMSVPGIQUKAE-UHFFFAOYSA-N 0.000 description 1
- WBRBKXDJEFBTPS-UHFFFAOYSA-N COc(ccc(C1CCC2)c3CCC1N2C(c1c(cccc2)c2ccc1)=O)c3OC Chemical compound COc(ccc(C1CCC2)c3CCC1N2C(c1c(cccc2)c2ccc1)=O)c3OC WBRBKXDJEFBTPS-UHFFFAOYSA-N 0.000 description 1
- OSEMOEIRGCDFLV-UHFFFAOYSA-N COc1c(C(CCC2)C(CC3)N2C(c(cc2)cc4c2[nH]cn4)=O)c3ccc1 Chemical compound COc1c(C(CCC2)C(CC3)N2C(c(cc2)cc4c2[nH]cn4)=O)c3ccc1 OSEMOEIRGCDFLV-UHFFFAOYSA-N 0.000 description 1
- MPOGNEQWFLEINN-UHFFFAOYSA-N COc1c2-c3cccnc3CCc2ccc1 Chemical compound COc1c2-c3cccnc3CCc2ccc1 MPOGNEQWFLEINN-UHFFFAOYSA-N 0.000 description 1
- JZDYTCUFSNWACA-YSSOQSIOSA-N C[C@@]12c3cc(C)ccc3CCC1NCCC2 Chemical compound C[C@@]12c3cc(C)ccc3CCC1NCCC2 JZDYTCUFSNWACA-YSSOQSIOSA-N 0.000 description 1
- LSLNLSFJUBTUFR-OZBJMMHXSA-N C[n]1c(ccc(C(N(CCC2)[C@@H](C3)C2c2c3cccc2)=O)c2)c2nc1 Chemical compound C[n]1c(ccc(C(N(CCC2)[C@@H](C3)C2c2c3cccc2)=O)c2)c2nc1 LSLNLSFJUBTUFR-OZBJMMHXSA-N 0.000 description 1
- HJSPEERCUCEKCJ-UHFFFAOYSA-N Cc(nn1)ccc1Oc1c(C2C(CC3)NCCC2)c3ccc1 Chemical compound Cc(nn1)ccc1Oc1c(C2C(CC3)NCCC2)c3ccc1 HJSPEERCUCEKCJ-UHFFFAOYSA-N 0.000 description 1
- KHWMGRISTVXPQI-UHFFFAOYSA-N Cc1cc2cc(C(N(CCC3)C4C3c3ccccc3C4)=O)ccc2[nH]1 Chemical compound Cc1cc2cc(C(N(CCC3)C4C3c3ccccc3C4)=O)ccc2[nH]1 KHWMGRISTVXPQI-UHFFFAOYSA-N 0.000 description 1
- SALMMXSVEDSOHE-UHFFFAOYSA-N N#Cc1cc(C(CCC2)C(CC3)N2C(c2ccc4[nH]cnc4c2)=O)c3cc1 Chemical compound N#Cc1cc(C(CCC2)C(CC3)N2C(c2ccc4[nH]cnc4c2)=O)c3cc1 SALMMXSVEDSOHE-UHFFFAOYSA-N 0.000 description 1
- VIBGVYWVPQKJGO-UHFFFAOYSA-N N#Cc1ccc(CCC2NCCCC22)c2c1 Chemical compound N#Cc1ccc(CCC2NCCCC22)c2c1 VIBGVYWVPQKJGO-UHFFFAOYSA-N 0.000 description 1
- VVZNCSHIBODHMZ-UZLBHIALSA-N N#Cc1ccc(C[C@@H]([C@@H]2CCC3)N3C(c(cc3)cc4c3[nH]cn4)=O)c2c1 Chemical compound N#Cc1ccc(C[C@@H]([C@@H]2CCC3)N3C(c(cc3)cc4c3[nH]cn4)=O)c2c1 VVZNCSHIBODHMZ-UZLBHIALSA-N 0.000 description 1
- WOLAGLMOWGJUJU-UHFFFAOYSA-N Nc([s]c1c2)nc1ccc2C(N(CCC1)C2C1c1ccccc1CC2)=O Chemical compound Nc([s]c1c2)nc1ccc2C(N(CCC1)C2C1c1ccccc1CC2)=O WOLAGLMOWGJUJU-UHFFFAOYSA-N 0.000 description 1
- MBBSEXKYQZBCGM-PKHIMPSTSA-N Nc(c(F)c1)ccc1C(N(CCC1)[C@@H]2C1c1ccccc1C2)=O Chemical compound Nc(c(F)c1)ccc1C(N(CCC1)[C@@H]2C1c1ccccc1C2)=O MBBSEXKYQZBCGM-PKHIMPSTSA-N 0.000 description 1
- HSVNIXYVLYCGJN-MRTLOADZSA-N Nc(cc1)ccc1C(N(CCC1)C(CC2)[C@H]1c1c2cccc1)=O Chemical compound Nc(cc1)ccc1C(N(CCC1)C(CC2)[C@H]1c1c2cccc1)=O HSVNIXYVLYCGJN-MRTLOADZSA-N 0.000 description 1
- LMVIQGMXPNRWGP-UHFFFAOYSA-N Nc1cc(C(N(CCC2)C3C2c2ccccc2CC3)=O)ccc1Cl Chemical compound Nc1cc(C(N(CCC2)C3C2c2ccccc2CC3)=O)ccc1Cl LMVIQGMXPNRWGP-UHFFFAOYSA-N 0.000 description 1
- ORFGTFOSNBQTJV-NEPJUHHUSA-N Nc1ccc([C@@H]2[C@H](C3)NCCC2)c3c1 Chemical compound Nc1ccc([C@@H]2[C@H](C3)NCCC2)c3c1 ORFGTFOSNBQTJV-NEPJUHHUSA-N 0.000 description 1
- DGWCPDMVXBWGCL-UHFFFAOYSA-N O=C(c1cc2ncc[n]2cc1)N(CCC1)C(C2)C1c1c2cccc1 Chemical compound O=C(c1cc2ncc[n]2cc1)N(CCC1)C(C2)C1c1c2cccc1 DGWCPDMVXBWGCL-UHFFFAOYSA-N 0.000 description 1
- WGSIBRJLMNRQCD-FHZUCYEKSA-N O=C(c1ccc(C(CCC2)[C@H](CC3)N2C(c2ccc4[nH]cnc4c2)=O)c3c1)N1CCCC1 Chemical compound O=C(c1ccc(C(CCC2)[C@H](CC3)N2C(c2ccc4[nH]cnc4c2)=O)c3c1)N1CCCC1 WGSIBRJLMNRQCD-FHZUCYEKSA-N 0.000 description 1
- ZOAXBNRBMBWPOC-UHFFFAOYSA-N O=C(c1ccc2[nH]cnc2c1)N(CCC1)C(CCc2ccc3)C1c2c3F Chemical compound O=C(c1ccc2[nH]cnc2c1)N(CCC1)C(CCc2ccc3)C1c2c3F ZOAXBNRBMBWPOC-UHFFFAOYSA-N 0.000 description 1
- NKSYBJUMTKTHRF-JWIMYKKASA-N O=C(c1ccc2[nH]cnc2c1)N(CCC1)[C@@H]2C1c1cc(C3CCCC3)ccc1C2 Chemical compound O=C(c1ccc2[nH]cnc2c1)N(CCC1)[C@@H]2C1c1cc(C3CCCC3)ccc1C2 NKSYBJUMTKTHRF-JWIMYKKASA-N 0.000 description 1
- LJPINMOPGGIXOP-UHFFFAOYSA-N O=C(c1ccccc1)N(CCC1)C2C1c1ccccc1CC2 Chemical compound O=C(c1ccccc1)N(CCC1)C2C1c1ccccc1CC2 LJPINMOPGGIXOP-UHFFFAOYSA-N 0.000 description 1
- GEBBHLKNKYHIJP-UHFFFAOYSA-N Oc(cc1)ccc1C(N(CCC1)C2C1c1ccccc1CC2)=O Chemical compound Oc(cc1)ccc1C(N(CCC1)C2C1c1ccccc1CC2)=O GEBBHLKNKYHIJP-UHFFFAOYSA-N 0.000 description 1
- USDYXUXFYLQEEU-UHFFFAOYSA-N Oc1c(C2C(CC3)NCCC2)c3ccc1 Chemical compound Oc1c(C2C(CC3)NCCC2)c3ccc1 USDYXUXFYLQEEU-UHFFFAOYSA-N 0.000 description 1
- MHRMWFCQRSOVJX-UHFFFAOYSA-N Oc1cccc(CC2)c1-c1c2nccc1 Chemical compound Oc1cccc(CC2)c1-c1c2nccc1 MHRMWFCQRSOVJX-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2010/055586 WO2011057054A1 (en) | 2009-11-06 | 2010-11-05 | Aryl- and heteroarylcarbonyl derivatives of hexahydroindenopyridine and octahydrobenzoquinoline |
| USPCT/US2010/055586 | 2010-11-05 | ||
| US201161484995P | 2011-05-11 | 2011-05-11 | |
| US61/484,995 | 2011-05-11 | ||
| PCT/US2011/059331 WO2012061708A1 (en) | 2010-11-05 | 2011-11-04 | Crystalline forms of hydrochloride salt of (4a-r,9a-s) -1- (1h - benzoimidazole- 5 -carbonyl) -2, 3, 4, 4a, 9, 9a - hexahydro -1h- indeno [2, 1 -b] pyridine- 6 -carbonitrile and their use as hsd 1 inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103228642A CN103228642A (zh) | 2013-07-31 |
| CN103228642B true CN103228642B (zh) | 2015-02-18 |
Family
ID=44999935
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201180053044.5A Expired - Fee Related CN103228642B (zh) | 2010-11-05 | 2011-11-04 | (4a-R,9a-S)-1-(1H-苯并咪唑-5-羰基)-2,3,4,4a,9,9a-六氢-1H-茚并[2,1-b]吡啶-6-甲腈盐酸盐的晶型及其作为HSD1抑制剂的用途 |
Country Status (36)
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CL2008003407A1 (es) | 2007-11-16 | 2010-01-11 | Boehringer Ingelheim Int | Compuestos derivados de aril- y heteroarilcarbonilo de heterobiciclo sustituido; composicion farmaceutica; procedimiento de preparacion; y su uso en el tratamiento y/o prevencion de trastornos metabolicos, mediado por la inhibicion de la enzima hsd-1. |
| US8765780B2 (en) | 2008-05-13 | 2014-07-01 | Boehringer Ingelheim International Gmbh | Alicyclic carboxylic acid derivatives of benzomorphans and related scaffolds, medicaments containing such compounds and their use |
| WO2010139673A1 (en) | 2009-06-02 | 2010-12-09 | Boehringer Ingelheim International Gmbh | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| EP2440537A1 (en) | 2009-06-11 | 2012-04-18 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 based on the 1,3 -oxazinan- 2 -one structure |
| US8933072B2 (en) | 2010-06-16 | 2015-01-13 | 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 |
| AU2013258109A1 (en) * | 2012-05-09 | 2014-10-30 | Boehringer Ingelheim International Gmbh | Pharmaceutical combinations for the treatment of metabolic disorders |
| EP3235813A1 (en) | 2016-04-19 | 2017-10-25 | Cidqo 2012, S.L. | Aza-tetra-cyclo derivatives |
| CN118206529A (zh) | 2017-09-04 | 2024-06-18 | C4医药公司 | 二氢苯并咪唑酮 |
| WO2020181232A1 (en) | 2019-03-06 | 2020-09-10 | C4 Therapeutics, Inc. | Heterocyclic compounds for medical treatment |
| CN118005644B (zh) * | 2024-01-29 | 2025-12-16 | 中国科学院南海海洋研究所 | 十氢芴型生物碱及其制备方法和在制备抗菌药物中应用 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009063061A3 (en) * | 2007-11-16 | 2009-07-23 | Boehringer Ingelheim Int | Aryl- and heteroarylcarbonyl derivatives of benzomorphanes and related scaffolds, medicaments containing such compounds and their use |
Family Cites Families (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL127995C (https=) | 1963-12-20 | Geigy Ag J R | ||
| US3341538A (en) | 1965-06-18 | 1967-09-12 | Geigy Chem Corp | Certain 2, 6-methano-3-benzazocines |
| DE1785124A1 (de) | 1968-08-13 | 1971-11-11 | Prym Werke William | Reissverschluss |
| DE2108954A1 (en) | 1971-02-25 | 1972-09-07 | Boehringer Sohn Ingelheim | 2-(furylmethyl)-6,7-benzomorphans - useful as cns active agents |
| GB1304175A (https=) | 1969-03-31 | 1973-01-24 | ||
| 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 |
| US3681349A (en) | 1970-03-05 | 1972-08-01 | Morton Norwich Products Inc | 1-(substituted benzyl) tetrahydro-2-(1h) pyrimidones |
| US3657257A (en) | 1970-08-31 | 1972-04-18 | Robins Co Inc A H | 3-aryl-8-carbamoyl nortropanes |
| 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 |
| DE2338369A1 (de) | 1973-07-26 | 1975-02-13 | Schering Ag | Mikrobiologische hydroxylierung von 2,6-methano-3-benzazocinen |
| SU510999A3 (ru) | 1973-10-27 | 1976-04-15 | К.Х.Берингер Зон, (Фирма) | Способ получени (метоксиметил-фурилметил)6,7-бензоморфанов илиморфинанов |
| US4009171A (en) | 1974-02-21 | 1977-02-22 | Sterling Drug Inc. | N-acylated-11-oxygenated-2,6-methano-3-benzazocine intermediates |
| 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 |
| DE2411382C3 (de) | 1974-03-09 | 1979-09-06 | C.H. Boehringer Sohn, 6507 Ingelheim | 2-Tetrahydrofurfuryl-6,7-benzomorphane, Verfahren zur Herstellung und deren Verwendung |
| DE2437610A1 (de) | 1974-08-05 | 1976-02-26 | Boehringer Sohn Ingelheim | Neue 5,9-beta-disubstituierte 2-tetrahydrofurfuryl-6,7-benzomorphane, deren saeureadditionssalze, ihre verwendung als arzneimittel und verfahren zu deren herstellung |
| US4108857A (en) | 1975-08-18 | 1978-08-22 | Sterling Drug Inc. | Imidazolylmethyl methanobenzazocines |
| 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 |
| GB9510459D0 (en) | 1995-05-24 | 1995-07-19 | Zeneca Ltd | Bicyclic amines |
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