JP2009533353A5 - - Google Patents
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- Publication number
- JP2009533353A5 JP2009533353A5 JP2009504476A JP2009504476A JP2009533353A5 JP 2009533353 A5 JP2009533353 A5 JP 2009533353A5 JP 2009504476 A JP2009504476 A JP 2009504476A JP 2009504476 A JP2009504476 A JP 2009504476A JP 2009533353 A5 JP2009533353 A5 JP 2009533353A5
- Authority
- JP
- Japan
- Prior art keywords
- spiro
- piperidine
- diethylaminocarbonyl
- compound
- benzopyran
- 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
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- 150000001875 compounds Chemical class 0.000 claims 83
- -1 carboxy, hydroxy Chemical group 0.000 claims 71
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 54
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 41
- 208000035475 disorder Diseases 0.000 claims 33
- 201000010099 disease Diseases 0.000 claims 21
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 21
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 11
- 239000008194 pharmaceutical composition Substances 0.000 claims 11
- 239000003814 drug Substances 0.000 claims 9
- 229940079593 drug Drugs 0.000 claims 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 7
- IJVCSMSMFSCRME-KBQPJGBKSA-N Dihydromorphine Chemical compound O([C@H]1[C@H](CC[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O IJVCSMSMFSCRME-KBQPJGBKSA-N 0.000 claims 6
- 208000023275 Autoimmune disease Diseases 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 5
- 208000011117 substance-related disease Diseases 0.000 claims 5
- 206010021639 Incontinence Diseases 0.000 claims 4
- DEXMFYZAHXMZNM-UHFFFAOYSA-N Narceine Chemical compound OC(=O)C1=C(OC)C(OC)=CC=C1C(=O)CC1=C(CCN(C)C)C=C(OCO2)C2=C1OC DEXMFYZAHXMZNM-UHFFFAOYSA-N 0.000 claims 4
- 210000003169 central nervous system Anatomy 0.000 claims 4
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 claims 4
- 230000000694 effects Effects 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 claims 4
- 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 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 238000002054 transplantation Methods 0.000 claims 4
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- 108090000137 Opioid Receptors Proteins 0.000 claims 3
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- 239000000203 mixture Substances 0.000 claims 3
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- 210000000056 organ Anatomy 0.000 claims 3
- 102000005962 receptors Human genes 0.000 claims 3
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- 231100000872 sexual dysfunction Toxicity 0.000 claims 3
- 208000016702 sympathetic nervous system disease Diseases 0.000 claims 3
- YQYVFVRQLZMJKJ-JBBXEZCESA-N (+)-cyclazocine Chemical compound C([C@@]1(C)C2=CC(O)=CC=C2C[C@@H]2[C@@H]1C)CN2CC1CC1 YQYVFVRQLZMJKJ-JBBXEZCESA-N 0.000 claims 2
- UVITTYOJFDLOGI-UHFFFAOYSA-N (1,2,5-trimethyl-4-phenylpiperidin-4-yl) propanoate Chemical compound C=1C=CC=CC=1C1(OC(=O)CC)CC(C)N(C)CC1C UVITTYOJFDLOGI-UHFFFAOYSA-N 0.000 claims 2
- TVYLLZQTGLZFBW-ZBFHGGJFSA-N (R,R)-tramadol Chemical compound COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-ZBFHGGJFSA-N 0.000 claims 2
- USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- 229940127291 Calcium channel antagonist Drugs 0.000 claims 2
- 206010011224 Cough Diseases 0.000 claims 2
- OGDVEMNWJVYAJL-LEPYJNQMSA-N Ethyl morphine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OCC OGDVEMNWJVYAJL-LEPYJNQMSA-N 0.000 claims 2
- OGDVEMNWJVYAJL-UHFFFAOYSA-N Ethylmorphine Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OCC OGDVEMNWJVYAJL-UHFFFAOYSA-N 0.000 claims 2
- 208000023783 Genitourinary tract disease Diseases 0.000 claims 2
- 208000010412 Glaucoma Diseases 0.000 claims 2
- GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 claims 2
- 206010020853 Hypertonic bladder Diseases 0.000 claims 2
- ALFGKMXHOUSVAD-UHFFFAOYSA-N Ketobemidone Chemical compound C=1C=CC(O)=CC=1C1(C(=O)CC)CCN(C)CC1 ALFGKMXHOUSVAD-UHFFFAOYSA-N 0.000 claims 2
- 229920006063 Lamide® Polymers 0.000 claims 2
- XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 claims 2
- IDBPHNDTYPBSNI-UHFFFAOYSA-N N-(1-(2-(4-Ethyl-5-oxo-2-tetrazolin-1-yl)ethyl)-4-(methoxymethyl)-4-piperidyl)propionanilide Chemical compound C1CN(CCN2C(N(CC)N=N2)=O)CCC1(COC)N(C(=O)CC)C1=CC=CC=C1 IDBPHNDTYPBSNI-UHFFFAOYSA-N 0.000 claims 2
- ONBWJWYUHXVEJS-ZTYRTETDSA-N Normorphine Chemical compound C([C@@H](NCC1)[C@@H]2C=C[C@@H]3O)C4=CC=C(O)C5=C4[C@@]21[C@H]3O5 ONBWJWYUHXVEJS-ZTYRTETDSA-N 0.000 claims 2
- 239000008896 Opium Substances 0.000 claims 2
- 208000009722 Overactive Urinary Bladder Diseases 0.000 claims 2
- BRUQQQPBMZOVGD-XFKAJCMBSA-N Oxycodone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C BRUQQQPBMZOVGD-XFKAJCMBSA-N 0.000 claims 2
- UQCNKQCJZOAFTQ-ISWURRPUSA-N Oxymorphone Chemical compound O([C@H]1C(CC[C@]23O)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O UQCNKQCJZOAFTQ-ISWURRPUSA-N 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 206010044565 Tremor Diseases 0.000 claims 2
- 208000000921 Urge Urinary Incontinence Diseases 0.000 claims 2
- 229960001391 alfentanil Drugs 0.000 claims 2
- 230000001430 anti-depressive effect Effects 0.000 claims 2
- 239000000935 antidepressant agent Substances 0.000 claims 2
- 229940005513 antidepressants Drugs 0.000 claims 2
- 239000000939 antiparkinson agent Substances 0.000 claims 2
- 239000003443 antiviral agent Substances 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 206010003119 arrhythmia Diseases 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- RDJGWRFTDZZXSM-RNWLQCGYSA-N benzylmorphine Chemical compound O([C@@H]1[C@]23CCN([C@H](C4)[C@@H]3C=C[C@@H]1O)C)C1=C2C4=CC=C1OCC1=CC=CC=C1 RDJGWRFTDZZXSM-RNWLQCGYSA-N 0.000 claims 2
- 229960001736 buprenorphine Drugs 0.000 claims 2
- RMRJXGBAOAMLHD-IHFGGWKQSA-N buprenorphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]11CC[C@]3([C@H](C1)[C@](C)(O)C(C)(C)C)OC)CN2CC1CC1 RMRJXGBAOAMLHD-IHFGGWKQSA-N 0.000 claims 2
- IFKLAQQSCNILHL-QHAWAJNXSA-N butorphanol Chemical compound N1([C@@H]2CC3=CC=C(C=C3[C@@]3([C@]2(CCCC3)O)CC1)O)CC1CCC1 IFKLAQQSCNILHL-QHAWAJNXSA-N 0.000 claims 2
- 229960001113 butorphanol Drugs 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 229960004126 codeine Drugs 0.000 claims 2
- 229950002213 cyclazocine Drugs 0.000 claims 2
- LNNWVNGFPYWNQE-GMIGKAJZSA-N desomorphine Chemical compound C1C2=CC=C(O)C3=C2[C@]24CCN(C)[C@H]1[C@@H]2CCC[C@@H]4O3 LNNWVNGFPYWNQE-GMIGKAJZSA-N 0.000 claims 2
- 229950003851 desomorphine Drugs 0.000 claims 2
- INUNXTSAACVKJS-OAQYLSRUSA-N dextromoramide Chemical compound C([C@@H](C)C(C(=O)N1CCCC1)(C=1C=CC=CC=1)C=1C=CC=CC=1)N1CCOCC1 INUNXTSAACVKJS-OAQYLSRUSA-N 0.000 claims 2
- 229960003701 dextromoramide Drugs 0.000 claims 2
- 229960004193 dextropropoxyphene Drugs 0.000 claims 2
- XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 claims 2
- 229960003461 dezocine Drugs 0.000 claims 2
- VTMVHDZWSFQSQP-VBNZEHGJSA-N dezocine Chemical compound C1CCCC[C@H]2CC3=CC=C(O)C=C3[C@]1(C)[C@H]2N VTMVHDZWSFQSQP-VBNZEHGJSA-N 0.000 claims 2
- 229960002069 diamorphine Drugs 0.000 claims 2
- XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 claims 2
- QIRAYNIFEOXSPW-UHFFFAOYSA-N dimepheptanol Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(O)CC)C1=CC=CC=C1 QIRAYNIFEOXSPW-UHFFFAOYSA-N 0.000 claims 2
- SVDHSZFEQYXRDC-UHFFFAOYSA-N dipipanone Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)CC)CC(C)N1CCCCC1 SVDHSZFEQYXRDC-UHFFFAOYSA-N 0.000 claims 2
- 229960002500 dipipanone Drugs 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 206010013663 drug dependence Diseases 0.000 claims 2
- ZOWQTJXNFTWSCS-IAQYHMDHSA-N eptazocine Chemical compound C1N(C)CC[C@@]2(C)C3=CC(O)=CC=C3C[C@@H]1C2 ZOWQTJXNFTWSCS-IAQYHMDHSA-N 0.000 claims 2
- 229950010920 eptazocine Drugs 0.000 claims 2
- 229960004578 ethylmorphine Drugs 0.000 claims 2
- 229960002428 fentanyl Drugs 0.000 claims 2
- PJMPHNIQZUBGLI-UHFFFAOYSA-N fentanyl Chemical compound C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 PJMPHNIQZUBGLI-UHFFFAOYSA-N 0.000 claims 2
- 230000007160 gastrointestinal dysfunction Effects 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- LLPOLZWFYMWNKH-CMKMFDCUSA-N hydrocodone Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)CC(=O)[C@@H]1OC1=C2C3=CC=C1OC LLPOLZWFYMWNKH-CMKMFDCUSA-N 0.000 claims 2
- 229960000240 hydrocodone Drugs 0.000 claims 2
- WVLOADHCBXTIJK-YNHQPCIGSA-N hydromorphone Chemical compound O([C@H]1C(CC[C@H]23)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O WVLOADHCBXTIJK-YNHQPCIGSA-N 0.000 claims 2
- 229960001410 hydromorphone Drugs 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 238000003384 imaging method Methods 0.000 claims 2
- 230000004957 immunoregulator effect Effects 0.000 claims 2
- IFKPLJWIEQBPGG-UHFFFAOYSA-N isomethadone Chemical compound C=1C=CC=CC=1C(C(C)CN(C)C)(C(=O)CC)C1=CC=CC=C1 IFKPLJWIEQBPGG-UHFFFAOYSA-N 0.000 claims 2
- 229950009272 isomethadone Drugs 0.000 claims 2
- 229960003029 ketobemidone Drugs 0.000 claims 2
- RCYBMSQOSGJZLO-BGWNEDDSSA-N levophenacylmorphan Chemical compound C([C@]12CCCC[C@H]1[C@H]1CC3=CC=C(C=C32)O)CN1CC(=O)C1=CC=CC=C1 RCYBMSQOSGJZLO-BGWNEDDSSA-N 0.000 claims 2
- IMYHGORQCPYVBZ-NLFFAJNJSA-N lofentanil Chemical compound CCC(=O)N([C@@]1([C@@H](CN(CCC=2C=CC=CC=2)CC1)C)C(=O)OC)C1=CC=CC=C1 IMYHGORQCPYVBZ-NLFFAJNJSA-N 0.000 claims 2
- 229950010274 lofentanil Drugs 0.000 claims 2
- 229960000365 meptazinol Drugs 0.000 claims 2
- JLICHNCFTLFZJN-HNNXBMFYSA-N meptazinol Chemical compound C=1C=CC(O)=CC=1[C@@]1(CC)CCCCN(C)C1 JLICHNCFTLFZJN-HNNXBMFYSA-N 0.000 claims 2
- YEOTYALSMRNXLJ-UHFFFAOYSA-N metazosin Chemical compound C1CN(C(=O)C(C)OC)CCN1C1=NC(N)=C(C=C(OC)C(OC)=C2)C2=N1 YEOTYALSMRNXLJ-UHFFFAOYSA-N 0.000 claims 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229960005181 morphine Drugs 0.000 claims 2
- 229960000805 nalbuphine Drugs 0.000 claims 2
- NETZHAKZCGBWSS-CEDHKZHLSA-N nalbuphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]1(O)CC[C@@H]3O)CN2CC1CCC1 NETZHAKZCGBWSS-CEDHKZHLSA-N 0.000 claims 2
- 229960004300 nicomorphine Drugs 0.000 claims 2
- HNDXBGYRMHRUFN-CIVUWBIHSA-N nicomorphine Chemical compound O([C@H]1C=C[C@H]2[C@H]3CC=4C5=C(C(=CC=4)OC(=O)C=4C=NC=CC=4)O[C@@H]1[C@]52CCN3C)C(=O)C1=CC=CN=C1 HNDXBGYRMHRUFN-CIVUWBIHSA-N 0.000 claims 2
- 229960004013 normethadone Drugs 0.000 claims 2
- WCJFBSYALHQBSK-UHFFFAOYSA-N normethadone Chemical compound C=1C=CC=CC=1C(CCN(C)C)(C(=O)CC)C1=CC=CC=C1 WCJFBSYALHQBSK-UHFFFAOYSA-N 0.000 claims 2
- 229950006134 normorphine Drugs 0.000 claims 2
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- VOKSWYLNZZRQPF-GDIGMMSISA-N pentazocine Chemical compound C1C2=CC=C(O)C=C2[C@@]2(C)[C@@H](C)[C@@H]1N(CC=C(C)C)CC2 VOKSWYLNZZRQPF-GDIGMMSISA-N 0.000 claims 2
- 229960005301 pentazocine Drugs 0.000 claims 2
- 229960000482 pethidine Drugs 0.000 claims 2
- LOXCOAXRHYDLOW-UHFFFAOYSA-N phenadoxone Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)CC)CC(C)N1CCOCC1 LOXCOAXRHYDLOW-UHFFFAOYSA-N 0.000 claims 2
- 229950004540 phenadoxone Drugs 0.000 claims 2
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- XJKQCILVUHXVIQ-UHFFFAOYSA-N properidine Chemical compound C=1C=CC=CC=1C1(C(=O)OC(C)C)CCN(C)CC1 XJKQCILVUHXVIQ-UHFFFAOYSA-N 0.000 claims 2
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- GGCSSNBKKAUURC-UHFFFAOYSA-N sufentanil Chemical group C1CN(CCC=2SC=CC=2)CCC1(COC)N(C(=O)CC)C1=CC=CC=C1 GGCSSNBKKAUURC-UHFFFAOYSA-N 0.000 claims 2
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- IVTMXOXVAHXCHI-YXLMWLKOSA-N (2s)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid;(2s)-3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic acid Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1.NN[C@@](C(O)=O)(C)CC1=CC=C(O)C(O)=C1 IVTMXOXVAHXCHI-YXLMWLKOSA-N 0.000 claims 1
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- 125000002947 alkylene group Chemical group 0.000 claims 1
- 230000007815 allergy Effects 0.000 claims 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims 1
- 229960003805 amantadine Drugs 0.000 claims 1
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- 239000002249 anxiolytic agent Substances 0.000 claims 1
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| KR20140015122A (ko) * | 2003-10-01 | 2014-02-06 | 아돌로 코포레이션 | 스피로시클릭 헤테로시클릭 유도체 및 이의 사용 방법 |
| US7576207B2 (en) * | 2006-04-06 | 2009-08-18 | Adolor Corporation | Spirocyclic heterocyclic derivatives and methods of their use |
| WO2008033299A2 (en) * | 2006-09-12 | 2008-03-20 | Adolor Corporation | Use of n-containing spirocompounds for the enhancement of cognitive function |
| FR2907121B1 (fr) * | 2006-10-12 | 2012-05-04 | Neorphys | Nouveaux derives morphiniques |
| JO3126B1 (ar) * | 2007-11-14 | 2017-09-20 | Janssen Pharmaceutica Nv | مثبطات ناقل نيوكليوسيد متوازن اي ان تي 1 |
| US9408837B2 (en) * | 2008-05-28 | 2016-08-09 | Kitov Pharmaceutical Ltd. | Ameliorating drug-induced elevations in blood pressure by adjunctive use of antihypertensive drugs |
| WO2013109521A1 (en) * | 2012-01-16 | 2013-07-25 | Vertex Pharmaceuticals Incorporated | Pyran-spirocyclic piperidine amides as modulators of ion channels |
| US10716784B2 (en) | 2013-03-07 | 2020-07-21 | Mindlab LLC | Pain medicine combination and uses thereof |
| CN110446533A (zh) * | 2016-09-13 | 2019-11-12 | 思想实验室有限责任公司 | 不宁腿综合征的药品组合与治疗 |
| CN110179988A (zh) * | 2019-07-10 | 2019-08-30 | 王大伟 | 五羟色胺再摄取抑制剂和单胺氧化酶抑制剂联合在制备治疗抑郁症或早泄药物中的应用 |
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-
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- 2007-04-05 AU AU2007234762A patent/AU2007234762A1/en not_active Abandoned
- 2007-04-05 WO PCT/US2007/066071 patent/WO2007118151A2/en not_active Ceased
- 2007-04-05 EP EP07760193A patent/EP2001467A4/en not_active Withdrawn
- 2007-04-05 MX MX2008012856A patent/MX2008012856A/es not_active Application Discontinuation
- 2007-04-05 BR BRPI0709466-3A patent/BRPI0709466A2/pt not_active IP Right Cessation
- 2007-04-05 JP JP2009504476A patent/JP2009533353A/ja active Pending
- 2007-04-05 KR KR1020087027224A patent/KR20090014157A/ko not_active Ceased
- 2007-04-05 CA CA002648287A patent/CA2648287A1/en not_active Abandoned
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2008
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- 2008-10-21 CO CO08112132A patent/CO6140027A2/es unknown
-
2009
- 2009-07-27 US US12/509,549 patent/US20100196269A1/en not_active Abandoned
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