NO312293B1 - Fremstilling av (S)-dekahydroisokinolin-3-karboksylsyre-t- butylamid, N-tert.-butyl-dekahydro-(4aS,8aS)-isokinolin-3 (S)-karboksamid og (R)-N-tert.-butyl-1,2,3,4-tetrahydro-3-isokinolinkarboksamid - Google Patents
Fremstilling av (S)-dekahydroisokinolin-3-karboksylsyre-t- butylamid, N-tert.-butyl-dekahydro-(4aS,8aS)-isokinolin-3 (S)-karboksamid og (R)-N-tert.-butyl-1,2,3,4-tetrahydro-3-isokinolinkarboksamid Download PDFInfo
- Publication number
- NO312293B1 NO312293B1 NO19983803A NO983803A NO312293B1 NO 312293 B1 NO312293 B1 NO 312293B1 NO 19983803 A NO19983803 A NO 19983803A NO 983803 A NO983803 A NO 983803A NO 312293 B1 NO312293 B1 NO 312293B1
- Authority
- NO
- Norway
- Prior art keywords
- reaction mixture
- tert
- butyl
- stated
- tetrahydro
- Prior art date
Links
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 11
- UPZBXVBPICTBDP-TUAOUCFPSA-N (3s,4as,8as)-n-tert-butyl-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxamide Chemical compound C1CCC[C@@H]2CN[C@H](C(=O)NC(C)(C)C)C[C@@H]21 UPZBXVBPICTBDP-TUAOUCFPSA-N 0.000 title claims description 6
- NSENYWQRQUNUGD-HACHORDNSA-N (3s)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylic acid Chemical compound C1CCCC2CN[C@H](C(=O)O)CC21 NSENYWQRQUNUGD-HACHORDNSA-N 0.000 title description 3
- 239000011541 reaction mixture Substances 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 41
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 18
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical group CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 16
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 16
- 239000003960 organic solvent Substances 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 11
- DMJXRYSGXCLCFP-LBPRGKRZSA-N (3s)-n-tert-butyl-1,2,3,4-tetrahydroisoquinoline-3-carboxamide Chemical compound C1=CC=C2CN[C@H](C(=O)NC(C)(C)C)CC2=C1 DMJXRYSGXCLCFP-LBPRGKRZSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000008346 aqueous phase Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- BWKMGYQJPOAASG-VIFPVBQESA-N (3s)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid Chemical compound C1=CC=C2CN[C@H](C(=O)O)CC2=C1 BWKMGYQJPOAASG-VIFPVBQESA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 150000003857 carboxamides Chemical class 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- DMJXRYSGXCLCFP-GFCCVEGCSA-N (3r)-n-tert-butyl-1,2,3,4-tetrahydroisoquinoline-3-carboxamide Chemical compound C1=CC=C2CN[C@@H](C(=O)NC(C)(C)C)CC2=C1 DMJXRYSGXCLCFP-GFCCVEGCSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000011260 aqueous acid Substances 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- BWKMGYQJPOAASG-SECBINFHSA-N D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid Chemical compound C1=CC=C2CN[C@@H](C(=O)O)CC2=C1 BWKMGYQJPOAASG-SECBINFHSA-N 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 2
- 229940011051 isopropyl acetate Drugs 0.000 claims description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 2
- 239000012074 organic phase Substances 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 230000005587 bubbling Effects 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 238000005984 hydrogenation reaction Methods 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical class NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229960005190 phenylalanine Drugs 0.000 description 3
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000003862 amino acid derivatives Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- RRONHWAVOYADJL-HNNXBMFYSA-N (2s)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 RRONHWAVOYADJL-HNNXBMFYSA-N 0.000 description 1
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical class C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- UGWULZWUXSCWPX-UHFFFAOYSA-N 2-sulfanylideneimidazolidin-4-one Chemical compound O=C1CNC(=S)N1 UGWULZWUXSCWPX-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N N-butylamine Natural products CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000001469 hydantoins Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Natural products C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- -1 isoquinoline compound Chemical class 0.000 description 1
- 150000002537 isoquinolines Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 150000003526 tetrahydroisoquinolines Chemical class 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/603,744 US5587481A (en) | 1996-02-20 | 1996-02-20 | Preparation of (S)-decahydroisoquinoline-3-carboxylic acid t-butylamide |
| PCT/US1996/016628 WO1997030976A1 (en) | 1996-02-20 | 1996-10-18 | Preparation of (s)-decahydroisoquinoline-3-carboxylic acid t-butylamide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO983803D0 NO983803D0 (no) | 1998-08-19 |
| NO983803L NO983803L (no) | 1998-10-19 |
| NO312293B1 true NO312293B1 (no) | 2002-04-22 |
Family
ID=24416734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19983803A NO312293B1 (no) | 1996-02-20 | 1998-08-19 | Fremstilling av (S)-dekahydroisokinolin-3-karboksylsyre-t- butylamid, N-tert.-butyl-dekahydro-(4aS,8aS)-isokinolin-3 (S)-karboksamid og (R)-N-tert.-butyl-1,2,3,4-tetrahydro-3-isokinolinkarboksamid |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5587481A (de) |
| EP (1) | EP0902781B1 (de) |
| JP (1) | JP2001506575A (de) |
| KR (1) | KR19990076981A (de) |
| AT (1) | ATE256664T1 (de) |
| AU (1) | AU713924B2 (de) |
| CA (1) | CA2238478A1 (de) |
| DE (1) | DE69631169T2 (de) |
| NO (1) | NO312293B1 (de) |
| WO (1) | WO1997030976A1 (de) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0751128B2 (de) † | 1995-06-30 | 2005-08-31 | Ajinomoto Co., Inc. | Verfahren zur Herstellung von optisch aktiven Amiden |
| IT1301825B1 (it) * | 1998-06-26 | 2000-07-07 | Archimica Spa | Procedimento per la preparazione di (s)-n-terbutil-1,2,3,4-tetraidroisochinolin-3-carbossiammide. |
| CZ299699B6 (cs) * | 1998-12-14 | 2008-10-22 | Sk Corporation | Zpusob výroby [3S-(3alfa, 4alfabeta, 8alfabeta)]-N-terc-butyl-dekahydro-3-izochinolinkarboxamidu s vysokým optickým výtežkem |
| KR100277723B1 (ko) * | 1998-12-14 | 2001-01-15 | 남창우 | 광학적으로 순수한 데카하이드로이소퀴놀린카르복사미드의 연속제조공정 |
| IT1313682B1 (it) * | 1999-11-25 | 2002-09-09 | Archimica Spa | Procedimento per la preparazione di (s)-n-terbutil-1,2,3,4-tetraidroisochinolin-3-carbossiammide. |
| IT1318986B1 (it) * | 2000-10-09 | 2003-09-19 | Archimica S P A Ora Clariant L | Procedimento per la preparazione di (s)-n-terbutil-1,2,3,4-tetraidroisochinolin-3-carbossiammide. |
| US8627573B2 (en) * | 2002-10-05 | 2014-01-14 | Braun Gmbh | Hair-removing device |
| JP2006525307A (ja) * | 2003-05-08 | 2006-11-09 | ファイザー インコーポレイテッド | Ｈｉｖ−プロテアーゼ阻害剤の合成に有用な中間体及びその製造法 |
| CN1300115C (zh) * | 2004-03-26 | 2007-02-14 | 厦门大学 | 一种合成1，2，3，4－四氢异喹啉衍生物的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1340588C (en) * | 1988-06-13 | 1999-06-08 | Balraj Krishan Handa | Amino acid derivatives |
| GB8927913D0 (en) * | 1989-12-11 | 1990-02-14 | Hoffmann La Roche | Amino acid derivatives |
| AU2228992A (en) * | 1991-07-08 | 1993-02-11 | Glaxo Group Limited | Thiazolidine derivatives and their use as anti-viral compounds |
| US5256783A (en) * | 1991-09-18 | 1993-10-26 | Hoffmann-La Roche Inc. | Method for producing 2-isoquinoline compounds |
| US5380849A (en) * | 1992-11-09 | 1995-01-10 | Merck & Co., Inc. | Process for optically pure decahydroisoqiunolines |
| EP0751128B2 (de) * | 1995-06-30 | 2005-08-31 | Ajinomoto Co., Inc. | Verfahren zur Herstellung von optisch aktiven Amiden |
-
1996
- 1996-02-20 US US08/603,744 patent/US5587481A/en not_active Expired - Lifetime
- 1996-10-18 KR KR1019980705110A patent/KR19990076981A/ko active IP Right Grant
- 1996-10-18 JP JP53011497A patent/JP2001506575A/ja active Pending
- 1996-10-18 EP EP96936615A patent/EP0902781B1/de not_active Expired - Lifetime
- 1996-10-18 AU AU74494/96A patent/AU713924B2/en not_active Ceased
- 1996-10-18 WO PCT/US1996/016628 patent/WO1997030976A1/en active IP Right Grant
- 1996-10-18 AT AT96936615T patent/ATE256664T1/de not_active IP Right Cessation
- 1996-10-18 CA CA002238478A patent/CA2238478A1/en not_active Abandoned
- 1996-10-18 DE DE69631169T patent/DE69631169T2/de not_active Expired - Fee Related
-
1998
- 1998-08-19 NO NO19983803A patent/NO312293B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2238478A1 (en) | 1997-08-28 |
| NO983803L (no) | 1998-10-19 |
| KR19990076981A (ko) | 1999-10-25 |
| US5587481A (en) | 1996-12-24 |
| JP2001506575A (ja) | 2001-05-22 |
| NO983803D0 (no) | 1998-08-19 |
| DE69631169T2 (de) | 2004-11-11 |
| EP0902781B1 (de) | 2003-12-17 |
| WO1997030976A1 (en) | 1997-08-28 |
| ATE256664T1 (de) | 2004-01-15 |
| EP0902781A4 (de) | 2000-07-19 |
| AU713924B2 (en) | 1999-12-16 |
| EP0902781A1 (de) | 1999-03-24 |
| AU7449496A (en) | 1997-09-10 |
| DE69631169D1 (de) | 2004-01-29 |
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