JP2018526387A5 - - Google Patents
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- JP2018526387A5 JP2018526387A5 JP2018511601A JP2018511601A JP2018526387A5 JP 2018526387 A5 JP2018526387 A5 JP 2018526387A5 JP 2018511601 A JP2018511601 A JP 2018511601A JP 2018511601 A JP2018511601 A JP 2018511601A JP 2018526387 A5 JP2018526387 A5 JP 2018526387A5
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- JP
- Japan
- Prior art keywords
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- producing
- subject
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 88
- 238000000034 method Methods 0.000 claims description 64
- 239000003638 chemical reducing agent Substances 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- ILJKKAIQFPEIBL-UHFFFAOYSA-N 2-cyclopropyl-2-hydroxyacetonitrile Chemical compound N#CC(O)C1CC1 ILJKKAIQFPEIBL-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 claims description 3
- KSNKQSPJFRQSEI-UHFFFAOYSA-N 3,3,3-trifluoropropanoic acid Chemical compound OC(=O)CC(F)(F)F KSNKQSPJFRQSEI-UHFFFAOYSA-N 0.000 claims description 2
- 208000000094 Chronic Pain Diseases 0.000 claims description 2
- 208000002193 Pain Diseases 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 208000004296 neuralgia Diseases 0.000 claims description 2
- 208000021722 neuropathic pain Diseases 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 238000012385 systemic delivery Methods 0.000 claims description 2
- 238000012384 transportation and delivery Methods 0.000 claims description 2
- 229930000680 A04AD01 - Scopolamine Natural products 0.000 claims 2
- STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 claims 2
- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 claims 2
- 230000001575 pathological effect Effects 0.000 claims 2
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 claims 2
- 229960002646 scopolamine Drugs 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- -1 sodium triacetoxyborohydride Chemical group 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 2
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical group [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562214727P | 2015-09-04 | 2015-09-04 | |
| US201562214734P | 2015-09-04 | 2015-09-04 | |
| US62/214,734 | 2015-09-04 | ||
| US62/214,727 | 2015-09-04 | ||
| PCT/US2016/049881 WO2017040770A1 (en) | 2015-09-04 | 2016-09-01 | Therapeutic compounds for pain and synthesis thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018526387A JP2018526387A (ja) | 2018-09-13 |
| JP2018526387A5 true JP2018526387A5 (https=) | 2018-11-01 |
| JP6736659B2 JP6736659B2 (ja) | 2020-08-05 |
Family
ID=58188341
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018511601A Expired - Fee Related JP6736659B2 (ja) | 2015-09-04 | 2016-09-01 | 疼痛のための治療化合物及びその合成 |
| JP2018511607A Expired - Fee Related JP6736661B2 (ja) | 2015-09-04 | 2016-09-01 | 治療化合物及び合成 |
| JP2018511605A Expired - Fee Related JP6736660B2 (ja) | 2015-09-04 | 2016-09-01 | 疼痛のための治療化合物及びその合成 |
| JP2018511626A Expired - Fee Related JP6868008B2 (ja) | 2015-09-04 | 2016-09-01 | 疼痛のための治療化合物及びその合成 |
| JP2018511670A Expired - Fee Related JP6639651B2 (ja) | 2015-09-04 | 2016-09-01 | 疼痛のための治療化合物及びその合成 |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018511607A Expired - Fee Related JP6736661B2 (ja) | 2015-09-04 | 2016-09-01 | 治療化合物及び合成 |
| JP2018511605A Expired - Fee Related JP6736660B2 (ja) | 2015-09-04 | 2016-09-01 | 疼痛のための治療化合物及びその合成 |
| JP2018511626A Expired - Fee Related JP6868008B2 (ja) | 2015-09-04 | 2016-09-01 | 疼痛のための治療化合物及びその合成 |
| JP2018511670A Expired - Fee Related JP6639651B2 (ja) | 2015-09-04 | 2016-09-01 | 疼痛のための治療化合物及びその合成 |
Country Status (11)
| Country | Link |
|---|---|
| US (9) | US10040797B2 (https=) |
| EP (5) | EP3344628B9 (https=) |
| JP (5) | JP6736659B2 (https=) |
| CN (5) | CN108495854B (https=) |
| CA (5) | CA2997545C (https=) |
| DK (4) | DK3344627T5 (https=) |
| ES (4) | ES2808048T3 (https=) |
| IL (5) | IL257732B (https=) |
| MA (1) | MA45011A (https=) |
| TW (11) | TWI641608B (https=) |
| WO (5) | WO2017040772A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2997545C (en) * | 2015-09-04 | 2022-01-11 | Janssen Pharmaceutica Nv | Therapeutic compounds for pain and synthesis thereof |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1469781A (en) * | 1974-06-10 | 1977-04-06 | Boehringer Sohn Ingelheim | Production of scopine |
| US4232026A (en) * | 1978-07-20 | 1980-11-04 | Merck & Co., Inc. | Diazaditwistanes, and pharmaceutical compositions for treating pain in warm blooded animals containing them |
| US4559157A (en) | 1983-04-21 | 1985-12-17 | Creative Products Resource Associates, Ltd. | Cosmetic applicator useful for skin moisturizing |
| LU84979A1 (fr) | 1983-08-30 | 1985-04-24 | Oreal | Composition cosmetique ou pharmaceutique sous forme aqueuse ou anhydre dont la phase grasse contient un polyether oligomere et polyethers oligomeres nouveaux |
| US4532244A (en) * | 1984-09-06 | 1985-07-30 | Innes Margaret N | Method of treating migraine headaches |
| US4820508A (en) | 1987-06-23 | 1989-04-11 | Neutrogena Corporation | Skin protective composition |
| US4992478A (en) | 1988-04-04 | 1991-02-12 | Warner-Lambert Company | Antiinflammatory skin moisturizing composition and method of preparing same |
| US4938949A (en) | 1988-09-12 | 1990-07-03 | University Of New York | Treatment of damaged bone marrow and dosage units therefor |
| ATE116317T1 (de) * | 1990-07-23 | 1995-01-15 | Pfizer | Chinuclidinderivate. |
| AU8906091A (en) | 1990-10-05 | 1992-04-28 | Wayne M. Barnes | Thermostable dna polymerase |
| US6432976B1 (en) * | 1999-10-29 | 2002-08-13 | Merck & Co., Inc. | 8-aza-bicyclo[3.2.1]octane NMDA/NR2B antagonists |
| DE10050994A1 (de) * | 2000-10-14 | 2002-04-18 | Boehringer Ingelheim Pharma | Neue als Arneimittel einsetzbare Anticholinergika sowie Verfahren zu deren Herstellung |
| DE602004021921D1 (de) * | 2003-05-28 | 2009-08-20 | Theravance Inc | Azabicycloalkanverbindungen als muscarinrezeptor antagonisten |
| WO2005037832A2 (en) * | 2003-10-15 | 2005-04-28 | Targacept, Inc. | Azabicycyclic compounds for relieving pain and treating central nervous system disorders |
| US7732607B2 (en) * | 2005-08-22 | 2010-06-08 | Anatoly Mazurov | Heteroaryl-substituted diazatricycloalkanes and methods of use thereof |
| US8735411B2 (en) * | 2006-10-02 | 2014-05-27 | Abbvie Inc. | Macrocyclic benzofused pyrimidine derivatives |
| WO2008104955A1 (en) * | 2007-02-28 | 2008-09-04 | Ranbaxy Laboratories Limited | Azoniatricyclo [3.3.1.0] nonane derivatives as muscarinic receptor antagonists |
| TW200840569A (en) * | 2007-03-13 | 2008-10-16 | Targacept Inc | Sub-type selective amides of diazabicycloalkanes |
| WO2009124755A1 (en) * | 2008-04-08 | 2009-10-15 | European Molecular Biology Laboratory (Embl) | Compounds with novel medical uses and method of identifying such compounds |
| CN101768158B (zh) * | 2010-01-04 | 2013-05-29 | 南昌弘益科技有限公司 | 噻托溴铵无水物及其制备方法 |
| CN102579458A (zh) * | 2012-03-08 | 2012-07-18 | 冀中能源峰峰集团有限公司总医院 | 缓解静点药物所致疼痛和防治静脉炎的药品配方 |
| JP6102122B2 (ja) * | 2012-08-24 | 2017-03-29 | ソニー株式会社 | 画像処理装置および方法、並びにプログラム |
| CN107098899B (zh) * | 2012-09-18 | 2019-09-06 | 赫普泰雅治疗有限公司 | 作为毒蕈碱的m1受体激动剂的二环氮杂化合物 |
| TW201444849A (zh) * | 2013-03-13 | 2014-12-01 | Janssen Pharmaceutica Nv | 經取代的7-氮雜雙環類及其作為食慾激素受體調節劑之用途 |
| JO3509B1 (ar) * | 2013-03-14 | 2020-07-05 | Janssen Pharmaceutica Nv | معدلات p2x7 |
| KR20160115503A (ko) * | 2015-03-27 | 2016-10-06 | 차의과학대학교 산학협력단 | 만성 골수성 백혈병 암 줄기세포의 성장 또는 증식 억제용 조성물 및 이의 스크리닝 방법 |
| GB201505654D0 (en) * | 2015-04-01 | 2015-05-13 | Nordic Bioscience As | Immunoassay for collagen type VI sequence |
| GB201505701D0 (en) * | 2015-04-02 | 2015-05-20 | Byotrol Plc | Anti-microbial composition |
| CA2997545C (en) * | 2015-09-04 | 2022-01-11 | Janssen Pharmaceutica Nv | Therapeutic compounds for pain and synthesis thereof |
-
2016
- 2016-09-01 CA CA2997545A patent/CA2997545C/en active Active
- 2016-09-01 US US15/254,960 patent/US10040797B2/en active Active
- 2016-09-01 US US15/254,965 patent/US10155762B2/en active Active
- 2016-09-01 ES ES16842975T patent/ES2808048T3/es active Active
- 2016-09-01 EP EP16842976.9A patent/EP3344628B9/en active Active
- 2016-09-01 ES ES16842973T patent/ES2807901T3/es active Active
- 2016-09-01 JP JP2018511601A patent/JP6736659B2/ja not_active Expired - Fee Related
- 2016-09-01 WO PCT/US2016/049885 patent/WO2017040772A1/en not_active Ceased
- 2016-09-01 US US15/254,944 patent/US9994572B2/en active Active
- 2016-09-01 CN CN201680064801.1A patent/CN108495854B/zh not_active Expired - Fee Related
- 2016-09-01 JP JP2018511607A patent/JP6736661B2/ja not_active Expired - Fee Related
- 2016-09-01 WO PCT/US2016/049877 patent/WO2017040767A1/en not_active Ceased
- 2016-09-01 DK DK16842975.1T patent/DK3344627T5/da active
- 2016-09-01 EP EP16842973.6A patent/EP3344626B9/en active Active
- 2016-09-01 CA CA2997430A patent/CA2997430C/en active Active
- 2016-09-01 US US15/254,952 patent/US10040796B2/en active Active
- 2016-09-01 JP JP2018511605A patent/JP6736660B2/ja not_active Expired - Fee Related
- 2016-09-01 CN CN201680064790.7A patent/CN108349934B/zh not_active Expired - Fee Related
- 2016-09-01 WO PCT/US2016/049881 patent/WO2017040770A1/en not_active Ceased
- 2016-09-01 MA MA045011A patent/MA45011A/fr unknown
- 2016-09-01 CN CN201680064789.4A patent/CN109071540B/zh not_active Expired - Fee Related
- 2016-09-01 CA CA2997541A patent/CA2997541C/en active Active
- 2016-09-01 DK DK16842971.0T patent/DK3344614T5/da active
- 2016-09-01 EP EP16842971.0A patent/EP3344614B9/en active Active
- 2016-09-01 ES ES16842971T patent/ES2809703T3/es active Active
- 2016-09-01 WO PCT/US2016/049893 patent/WO2017040778A1/en not_active Ceased
- 2016-09-01 DK DK16842973.6T patent/DK3344626T5/da active
- 2016-09-01 CN CN201680064673.0A patent/CN108290890B/zh not_active Expired - Fee Related
- 2016-09-01 US US15/254,938 patent/US10040795B2/en active Active
- 2016-09-01 ES ES16842976T patent/ES2812233T3/es active Active
- 2016-09-01 EP EP16842981.9A patent/EP3344629A4/en not_active Withdrawn
- 2016-09-01 CA CA2997501A patent/CA2997501C/en active Active
- 2016-09-01 CN CN201680064788.XA patent/CN109153679B/zh not_active Expired - Fee Related
- 2016-09-01 WO PCT/US2016/049871 patent/WO2017040764A1/en not_active Ceased
- 2016-09-01 DK DK16842976.9T patent/DK3344628T5/da active
- 2016-09-01 JP JP2018511626A patent/JP6868008B2/ja not_active Expired - Fee Related
- 2016-09-01 EP EP16842975.1A patent/EP3344627B9/en active Active
- 2016-09-01 CA CA2997543A patent/CA2997543C/en active Active
- 2016-09-01 JP JP2018511670A patent/JP6639651B2/ja not_active Expired - Fee Related
- 2016-09-02 TW TW105128533A patent/TWI641608B/zh not_active IP Right Cessation
- 2016-09-02 TW TW108103711A patent/TWI683815B/zh not_active IP Right Cessation
- 2016-09-02 TW TW107128718A patent/TWI713879B/zh not_active IP Right Cessation
- 2016-09-02 TW TW107101163A patent/TWI672303B/zh not_active IP Right Cessation
- 2016-09-02 TW TW105128531A patent/TWI663167B/zh not_active IP Right Cessation
- 2016-09-02 TW TW106142501A patent/TWI695836B/zh not_active IP Right Cessation
- 2016-09-02 TW TW105128530A patent/TWI636054B/zh not_active IP Right Cessation
- 2016-09-02 TW TW105128528A patent/TWI654188B/zh not_active IP Right Cessation
- 2016-09-02 TW TW105128529A patent/TWI639597B/zh not_active IP Right Cessation
- 2016-09-02 TW TW107117875A patent/TWI686393B/zh not_active IP Right Cessation
- 2016-09-02 TW TW107120678A patent/TWI707854B/zh not_active IP Right Cessation
-
2018
- 2018-02-26 IL IL257732A patent/IL257732B/en active IP Right Grant
- 2018-02-26 IL IL257735A patent/IL257735B/en unknown
- 2018-02-26 IL IL257737A patent/IL257737B2/en unknown
- 2018-02-26 IL IL257740A patent/IL257740A/en active IP Right Grant
- 2018-02-26 IL IL257734A patent/IL257734B/en unknown
- 2018-06-11 US US16/005,366 patent/US10351565B2/en active Active
- 2018-07-24 US US16/043,829 patent/US10358448B2/en active Active
- 2018-07-24 US US16/043,813 patent/US10351566B2/en active Active
- 2018-12-17 US US16/222,852 patent/US10766898B2/en not_active Expired - Fee Related
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