NO317302B1 - Forbedret fremgangsmate for fremstilling av farmasoytisk verdifulle norbenzomorfan-derivater - Google Patents
Forbedret fremgangsmate for fremstilling av farmasoytisk verdifulle norbenzomorfan-derivater Download PDFInfo
- Publication number
- NO317302B1 NO317302B1 NO20005818A NO20005818A NO317302B1 NO 317302 B1 NO317302 B1 NO 317302B1 NO 20005818 A NO20005818 A NO 20005818A NO 20005818 A NO20005818 A NO 20005818A NO 317302 B1 NO317302 B1 NO 317302B1
- Authority
- NO
- Norway
- Prior art keywords
- acid
- aluminum
- reaction
- piperidine
- process according
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 title description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 22
- -1 C 1 -C 5 alkoxy Chemical group 0.000 claims description 20
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 150000003053 piperidines Chemical class 0.000 claims description 6
- 239000012429 reaction media Substances 0.000 claims description 6
- 239000000203 mixture Chemical class 0.000 claims description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 4
- UQDFPUOBXNBENB-UHFFFAOYSA-N 2-[(3-methoxyphenyl)methyl]-3,3-dimethyl-4-methylidenepiperidine Chemical compound COC1=CC=CC(CC2C(C(=C)CCN2)(C)C)=C1 UQDFPUOBXNBENB-UHFFFAOYSA-N 0.000 claims description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- LPKIGDXRQSIQBA-UHFFFAOYSA-N 4-methylidenepiperidine Chemical class C=C1CCNCC1 LPKIGDXRQSIQBA-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000001555 benzenes Chemical class 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 2
- 229910052782 aluminium Inorganic materials 0.000 claims 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- DNNGHKHJLRIZJA-UHFFFAOYSA-N 2-[(2-methoxyphenyl)methyl]-3,3-dimethyl-4-methylidenepiperidine Chemical compound COC1=CC=CC=C1CC1C(C)(C)C(=C)CCN1 DNNGHKHJLRIZJA-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229940095064 tartrate Drugs 0.000 description 2
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
- 239000001358 L(+)-tartaric acid Substances 0.000 description 1
- 235000011002 L(+)-tartaric acid Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-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
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000005661 deetherification reaction Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
- C07D221/26—Benzomorphans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19822822A DE19822822A1 (de) | 1998-05-20 | 1998-05-20 | Verbessertes Verfahren zur Herstellung von pharmazeutisch wertvollen Norbenzomorphanderivaten |
| PCT/EP1999/003142 WO1999059976A1 (de) | 1998-05-20 | 1999-05-07 | Verbessertes verfahren zur herstellung von pharmazeutisch wertvollen norbenzomorphanderivaten |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20005818L NO20005818L (no) | 2000-11-17 |
| NO20005818D0 NO20005818D0 (no) | 2000-11-17 |
| NO317302B1 true NO317302B1 (no) | 2004-10-04 |
Family
ID=7868527
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20005818A NO317302B1 (no) | 1998-05-20 | 2000-11-17 | Forbedret fremgangsmate for fremstilling av farmasoytisk verdifulle norbenzomorfan-derivater |
Country Status (38)
| Country | Link |
|---|---|
| US (1) | US6124459A (xx) |
| EP (1) | EP1080076B1 (xx) |
| JP (1) | JP4526185B2 (xx) |
| KR (1) | KR20010043703A (xx) |
| CN (1) | CN1113058C (xx) |
| AR (1) | AR016040A1 (xx) |
| AT (1) | ATE254605T1 (xx) |
| AU (1) | AU753563B2 (xx) |
| BG (1) | BG104964A (xx) |
| BR (1) | BR9910603A (xx) |
| CA (1) | CA2330669C (xx) |
| CO (1) | CO5060460A1 (xx) |
| DE (2) | DE19822822A1 (xx) |
| DK (1) | DK1080076T3 (xx) |
| EA (1) | EA003059B1 (xx) |
| EE (1) | EE04305B1 (xx) |
| EG (1) | EG21526A (xx) |
| ES (1) | ES2211093T3 (xx) |
| HK (1) | HK1035728A1 (xx) |
| HR (1) | HRP20000793A2 (xx) |
| HU (1) | HUP0102034A3 (xx) |
| ID (1) | ID27014A (xx) |
| IL (1) | IL138998A0 (xx) |
| MY (1) | MY120806A (xx) |
| NO (1) | NO317302B1 (xx) |
| NZ (1) | NZ508845A (xx) |
| PE (1) | PE20000558A1 (xx) |
| PL (1) | PL343935A1 (xx) |
| PT (1) | PT1080076E (xx) |
| SI (1) | SI1080076T1 (xx) |
| SK (1) | SK283996B6 (xx) |
| TR (1) | TR200003360T2 (xx) |
| TW (1) | TW455582B (xx) |
| UA (1) | UA59448C2 (xx) |
| UY (1) | UY25515A1 (xx) |
| WO (1) | WO1999059976A1 (xx) |
| YU (1) | YU71400A (xx) |
| ZA (1) | ZA200005740B (xx) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7405149B1 (en) * | 1998-12-21 | 2008-07-29 | Megica Corporation | Post passivation method for semiconductor chip or wafer |
| WO2016044546A1 (en) * | 2014-09-17 | 2016-03-24 | Purdue Pharma L.P. | Benzomorphan analogs and the use thereof |
| CN107089948B (zh) * | 2017-04-28 | 2020-07-17 | 云南大学 | 吗吩衍生物及其制备方法和应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE34235B1 (en) * | 1969-06-04 | 1975-03-19 | Acf Chemiefarma Nv | 6,7-benzomorphans and their preparation |
| US4255579A (en) * | 1974-05-20 | 1981-03-10 | Sterling Drug Inc. | 11-Substituted hexahydro-2,6-methano-3-benzazocines |
| US3932422A (en) * | 1974-05-20 | 1976-01-13 | Sterling Drug Inc. | 8-Methylene-3-azabicyclo[3.3.1]non-6-en-4-ones |
| DE19528472A1 (de) * | 1995-08-03 | 1997-02-06 | Boehringer Ingelheim Kg | Neues Verfahren zur Herstellung von Norbenzomorphan einer Zwischenstufe bei Herstellung von pharmazeutisch wertvollen Benzomorphanderivaten, insbesondere von (-)-(1R,5S,S"R)-3'-Hydroxy-2-(2-methoxypropyl-)-5,9,9-trimethyl-6,7 benzomorphan |
-
1998
- 1998-05-20 DE DE19822822A patent/DE19822822A1/de not_active Withdrawn
-
1999
- 1999-05-07 SI SI9930488T patent/SI1080076T1/xx unknown
- 1999-05-07 NZ NZ508845A patent/NZ508845A/xx unknown
- 1999-05-07 CN CN99806339A patent/CN1113058C/zh not_active Expired - Fee Related
- 1999-05-07 HU HU0102034A patent/HUP0102034A3/hu unknown
- 1999-05-07 AT AT99924901T patent/ATE254605T1/de not_active IP Right Cessation
- 1999-05-07 AU AU41399/99A patent/AU753563B2/en not_active Ceased
- 1999-05-07 CA CA002330669A patent/CA2330669C/en not_active Expired - Fee Related
- 1999-05-07 IL IL13899899A patent/IL138998A0/xx unknown
- 1999-05-07 DK DK99924901T patent/DK1080076T3/da active
- 1999-05-07 KR KR1020007012923A patent/KR20010043703A/ko not_active Application Discontinuation
- 1999-05-07 PL PL99343935A patent/PL343935A1/xx not_active IP Right Cessation
- 1999-05-07 JP JP2000549595A patent/JP4526185B2/ja not_active Expired - Fee Related
- 1999-05-07 TR TR2000/03360T patent/TR200003360T2/xx unknown
- 1999-05-07 ES ES99924901T patent/ES2211093T3/es not_active Expired - Lifetime
- 1999-05-07 EP EP99924901A patent/EP1080076B1/de not_active Expired - Lifetime
- 1999-05-07 DE DE59907804T patent/DE59907804D1/de not_active Expired - Lifetime
- 1999-05-07 ID IDW20002394A patent/ID27014A/id unknown
- 1999-05-07 WO PCT/EP1999/003142 patent/WO1999059976A1/de not_active Application Discontinuation
- 1999-05-07 PT PT99924901T patent/PT1080076E/pt unknown
- 1999-05-07 YU YU71400A patent/YU71400A/sh unknown
- 1999-05-07 SK SK1731-2000A patent/SK283996B6/sk unknown
- 1999-05-07 EA EA200001212A patent/EA003059B1/ru not_active IP Right Cessation
- 1999-05-07 BR BR9910603-5A patent/BR9910603A/pt not_active IP Right Cessation
- 1999-05-07 EE EEP200000674A patent/EE04305B1/xx not_active IP Right Cessation
- 1999-05-17 US US09/313,001 patent/US6124459A/en not_active Expired - Lifetime
- 1999-05-17 EG EG56999A patent/EG21526A/xx active
- 1999-05-17 PE PE1999000413A patent/PE20000558A1/es not_active Application Discontinuation
- 1999-05-18 CO CO99030491A patent/CO5060460A1/es unknown
- 1999-05-18 TW TW088108090A patent/TW455582B/zh not_active IP Right Cessation
- 1999-05-18 UY UY25515A patent/UY25515A1/es not_active IP Right Cessation
- 1999-05-19 MY MYPI99001967A patent/MY120806A/en unknown
- 1999-05-19 AR ARP990102374A patent/AR016040A1/es not_active Suspension/Interruption
- 1999-07-05 UA UA2000127360A patent/UA59448C2/uk unknown
-
2000
- 2000-10-17 ZA ZA200005740A patent/ZA200005740B/xx unknown
- 2000-11-17 NO NO20005818A patent/NO317302B1/no unknown
- 2000-11-17 HR HR20000793A patent/HRP20000793A2/hr not_active Application Discontinuation
- 2000-11-17 BG BG104964A patent/BG104964A/xx active Pending
-
2001
- 2001-09-12 HK HK01106427A patent/HK1035728A1/xx not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3055819B2 (ja) | ２−チエニルグリシド酸誘導体およびその製造法 | |
| WO2014026657A2 (en) | A process for the preparation of a derivative of 2-methyl-2'-phenylpropionic acid using new intermediates | |
| NO120686B (xx) | ||
| US10544101B2 (en) | Process for the preparation of butorphanol tartrate | |
| Neumeyer et al. | Aporphines. 9. Synthesis and Pharmacological Evaluation of (±) 9, 10-Dihydroxyaporphine [(±)-Isoapomorphine],(±)-,(-)-, and (±)-1, 2-Dihydroxyaporphine, and (+)-1, 2, 9, 10-Tetrahydroxyaporphine. | |
| NO317302B1 (no) | Forbedret fremgangsmate for fremstilling av farmasoytisk verdifulle norbenzomorfan-derivater | |
| JPS6113472B2 (xx) | ||
| KR100399669B1 (ko) | 약제학적으로유용한벤조모르판유도체제조시의중간체인노르벤조모르판,특히(-)-(1r,5s,2'r)-3'-하이드록시-2-(2-메톡시프로필)-5,9,9-트리메틸-6,7-벤조모르판을제조하는방법 | |
| IL46440A (en) | Xanthene-9-spiro-4'-piperidine and some derivatives thereof | |
| AU2002233708B2 (en) | Process for producing quinoline-3-carboxylic acid compound | |
| JP2022055368A (ja) | ベンゾアゼピン誘導体の製造方法及びその中間体 | |
| EP1366034B1 (en) | Preparation of phthalanes | |
| KR101625128B1 (ko) | 3,4-디메톡시바이사이클로[4.2.0]옥타-1,3,5-트리엔-7-카보니트릴의 합성 방법, 및 이바브라딘 및 이의 약제학적으로 허용되는 산과의 부가염의 합성에서의 적용 | |
| MXPA00010964A (en) | Improved method for preparing pharmaceutically valuable norbenzomorphane derivatives | |
| EP3280701A1 (en) | A method of chiral resolution of the key intermediate of the synthesis of apremilast and its use for the preparation of pure apremilast | |
| KR930010500B1 (ko) | 코타르닌의 제조방법 | |
| NO144099B (no) | Dyse for maskinell flammehoevling av enkelte defekter paa overflaten til et metallegeme | |
| CZ20004323A3 (cs) | Způsob výroby R- a S- norbenzomorfanů | |
| Kaslow et al. | SUBSTITUTED PHENYLQUINOLINES1 | |
| US3118900A (en) | Substituted derivatives of 3-aza-6, 7-benzo-8-oxa-5-phenylbicyclo[3.3.1]-nonane | |
| NO781896L (no) | 4-fenyl-8-amino-tetrahydroisokinoliner, farmasoeytiske preparater som inneholder disse, fremgangsmaate til fremstilling av disse preparater og deres anvendelse som antidepresjonsmidler | |
| JP4011819B2 (ja) | インドール誘導体の製造法およびその中間体 | |
| BG60660B2 (bg) | ПРОИЗВОДНИ НА ПИРАНО/3,4-b/ИНДОЛА,ФАРМАЦЕВТИЧНИ СЪСТАВИ И МЕТОДИ НА ПРИЛОЖЕНИЕ | |
| US20040192919A1 (en) | Process for production of highly pure donepezil hydrochloride | |
| NO143785B (no) | Fremgangsmaate for varmekstrudering av aluminiumlegeringer med hoey strekkfasthet |