NO312761B1 - Fremgangsmåte for fremstilling av tetrahydroisokinoliner og beslektede heterosykliske forbindelser - Google Patents
Fremgangsmåte for fremstilling av tetrahydroisokinoliner og beslektede heterosykliske forbindelser Download PDFInfo
- Publication number
- NO312761B1 NO312761B1 NO19991495A NO991495A NO312761B1 NO 312761 B1 NO312761 B1 NO 312761B1 NO 19991495 A NO19991495 A NO 19991495A NO 991495 A NO991495 A NO 991495A NO 312761 B1 NO312761 B1 NO 312761B1
- Authority
- NO
- Norway
- Prior art keywords
- formaldehyde
- alkyl
- compound
- lewis acid
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000003526 tetrahydroisoquinolines Chemical class 0.000 title description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 3
- 230000008569 process Effects 0.000 title description 2
- 239000002841 Lewis acid Substances 0.000 claims description 10
- 150000007517 lewis acids Chemical class 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 8
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical group COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 claims description 7
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 6
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 6
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- -1 C1-4 -Alkoxy Chemical group 0.000 claims description 4
- 239000011592 zinc chloride Substances 0.000 claims description 4
- 235000005074 zinc chloride Nutrition 0.000 claims description 4
- LOCDPORVFVOGCR-UHFFFAOYSA-N Bis(methylthio)methane Chemical compound CSCSC LOCDPORVFVOGCR-UHFFFAOYSA-N 0.000 claims description 3
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 claims description 3
- 229910001623 magnesium bromide Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229920002866 paraformaldehyde Polymers 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- UKGKVQZMKWBQDH-UHFFFAOYSA-N 2-benzylsulfonyl-3,3-dimethyl-1,4-dihydroisoquinoline Chemical compound C(C1=CC=CC=C1)S(=O)(=O)N1CC2=CC=CC=C2CC1(C)C UKGKVQZMKWBQDH-UHFFFAOYSA-N 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 3
- 101150041968 CDC13 gene Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KAMDOKUMNIDGGT-UHFFFAOYSA-N N-(2-methyl-1-phenylpropan-2-yl)-1-phenylmethanesulfonamide Chemical compound C(C1=CC=CC=C1)S(=O)(=O)NC(CC1=CC=CC=C1)(C)C KAMDOKUMNIDGGT-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 230000000451 tissue damage Effects 0.000 description 2
- 231100000827 tissue damage Toxicity 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- LTJQRZGEPZQDLX-UHFFFAOYSA-N 3,3-dimethyl-2,4-dihydro-1h-isoquinoline Chemical compound C1=CC=C2CNC(C)(C)CC2=C1 LTJQRZGEPZQDLX-UHFFFAOYSA-N 0.000 description 1
- FXQNTOHRTXRWTM-UHFFFAOYSA-N 3,3-dimethyl-4h-isoquinoline Chemical compound C1=CC=C2C=NC(C)(C)CC2=C1 FXQNTOHRTXRWTM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical class NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- 238000006929 Pictet-Spengler synthesis reaction Methods 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 230000002292 Radical scavenging effect Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 238000007336 electrophilic substitution reaction Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity 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
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- QLUMLEDLZDMGDW-UHFFFAOYSA-N sodium;1h-naphthalen-1-ide Chemical compound [Na+].[C-]1=CC=CC2=CC=CC=C21 QLUMLEDLZDMGDW-UHFFFAOYSA-N 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
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
- C07D217/18—Aralkyl radicals
- C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72258896A | 1996-09-27 | 1996-09-27 | |
| PCT/US1997/013672 WO1998013351A1 (fr) | 1996-09-27 | 1997-08-04 | Reaction de pictet-spengler pour la synthese des tetrahydro-isoquinolines et composes heterocycliques associes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO991495D0 NO991495D0 (no) | 1999-03-26 |
| NO991495L NO991495L (no) | 1999-03-26 |
| NO312761B1 true NO312761B1 (no) | 2002-07-01 |
Family
ID=24902494
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19991495A NO312761B1 (no) | 1996-09-27 | 1999-03-26 | Fremgangsmåte for fremstilling av tetrahydroisokinoliner og beslektede heterosykliske forbindelser |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP0929527B1 (fr) |
| JP (1) | JP2001510449A (fr) |
| KR (1) | KR100445953B1 (fr) |
| CN (1) | CN1101811C (fr) |
| AR (1) | AR009364A1 (fr) |
| AT (1) | ATE280761T1 (fr) |
| AU (1) | AU711358B2 (fr) |
| BR (1) | BR9712143B1 (fr) |
| CA (1) | CA2266357C (fr) |
| DE (1) | DE69731392T2 (fr) |
| DK (1) | DK0929527T3 (fr) |
| ES (1) | ES2230618T3 (fr) |
| HK (1) | HK1022311A1 (fr) |
| HU (1) | HUP9904161A3 (fr) |
| IL (1) | IL129188A (fr) |
| NO (1) | NO312761B1 (fr) |
| NZ (1) | NZ334491A (fr) |
| PT (1) | PT929527E (fr) |
| SI (1) | SI0929527T1 (fr) |
| TW (1) | TW434224B (fr) |
| WO (1) | WO1998013351A1 (fr) |
| ZA (1) | ZA978560B (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100503571C (zh) * | 2006-07-12 | 2009-06-24 | 中国药科大学 | 四氢异喹啉类衍生物、其制备方法及其医药用途 |
| EP2420237A1 (fr) | 2010-08-11 | 2012-02-22 | Ville Takio | Dérivés fluorés d'isoquinoléines endogènes pour leur utilisation dans le traitement de maladies liées aux passages d'isoquinoline endogène |
| CN103694170B (zh) * | 2013-04-01 | 2016-04-06 | 常州夏青化工有限公司 | 6,7-二氟-1-甲基-1,2,3,4-四氢异喹啉盐酸盐的合成方法 |
| CN110590795B (zh) * | 2019-10-10 | 2021-01-22 | 贵州省中国科学院天然产物化学重点实验室(贵州医科大学天然产物化学重点实验室) | 一类多并杂环螺羟吲哚类化合物的合成方法 |
| FI130627B (en) | 2021-03-31 | 2023-12-18 | Equinorm Ltd | NEW HETEROCYCLIC COMPOUNDS AND THEIR USE |
| CN113214252B (zh) * | 2021-05-28 | 2022-02-11 | 常州大学 | 6-苯基-7-(吡啶-2-基)-7H-吲哚并[2,3-c]喹啉化合物的合成方法 |
-
1997
- 1997-08-04 IL IL12918897A patent/IL129188A/en not_active IP Right Cessation
- 1997-08-04 CN CN97198263A patent/CN1101811C/zh not_active Expired - Fee Related
- 1997-08-04 PT PT97936381T patent/PT929527E/pt unknown
- 1997-08-04 NZ NZ334491A patent/NZ334491A/xx unknown
- 1997-08-04 HU HU9904161A patent/HUP9904161A3/hu unknown
- 1997-08-04 AT AT97936381T patent/ATE280761T1/de not_active IP Right Cessation
- 1997-08-04 WO PCT/US1997/013672 patent/WO1998013351A1/fr active IP Right Grant
- 1997-08-04 AU AU39063/97A patent/AU711358B2/en not_active Ceased
- 1997-08-04 CA CA002266357A patent/CA2266357C/fr not_active Expired - Fee Related
- 1997-08-04 SI SI9730683T patent/SI0929527T1/xx unknown
- 1997-08-04 DK DK97936381T patent/DK0929527T3/da active
- 1997-08-04 DE DE69731392T patent/DE69731392T2/de not_active Expired - Fee Related
- 1997-08-04 ES ES97936381T patent/ES2230618T3/es not_active Expired - Lifetime
- 1997-08-04 KR KR10-1999-7002580A patent/KR100445953B1/ko not_active IP Right Cessation
- 1997-08-04 BR BRPI9712143-6A patent/BR9712143B1/pt not_active IP Right Cessation
- 1997-08-04 JP JP51562398A patent/JP2001510449A/ja not_active Ceased
- 1997-08-04 EP EP97936381A patent/EP0929527B1/fr not_active Expired - Lifetime
- 1997-09-17 AR ARP970104243A patent/AR009364A1/es active IP Right Grant
- 1997-09-23 TW TW086113858A patent/TW434224B/zh not_active IP Right Cessation
- 1997-09-23 ZA ZA9708560A patent/ZA978560B/xx unknown
-
1999
- 1999-03-26 NO NO19991495A patent/NO312761B1/no not_active IP Right Cessation
-
2000
- 2000-02-28 HK HK00101202A patent/HK1022311A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PT929527E (pt) | 2005-01-31 |
| NO991495D0 (no) | 1999-03-26 |
| CN1101811C (zh) | 2003-02-19 |
| TW434224B (en) | 2001-05-16 |
| DK0929527T3 (da) | 2005-02-14 |
| HK1022311A1 (en) | 2000-08-04 |
| DE69731392D1 (de) | 2004-12-02 |
| AU3906397A (en) | 1998-04-17 |
| BR9712143A (pt) | 1999-08-31 |
| BR9712143B1 (pt) | 2009-05-05 |
| IL129188A0 (en) | 2000-02-17 |
| DE69731392T2 (de) | 2006-02-09 |
| NZ334491A (en) | 2000-04-28 |
| EP0929527A1 (fr) | 1999-07-21 |
| NO991495L (no) | 1999-03-26 |
| ES2230618T3 (es) | 2005-05-01 |
| KR20000048638A (ko) | 2000-07-25 |
| IL129188A (en) | 2004-03-28 |
| HUP9904161A3 (en) | 2001-01-29 |
| KR100445953B1 (ko) | 2004-08-25 |
| EP0929527B1 (fr) | 2004-10-27 |
| JP2001510449A (ja) | 2001-07-31 |
| AR009364A1 (es) | 2000-04-12 |
| ZA978560B (en) | 1998-03-27 |
| CN1231660A (zh) | 1999-10-13 |
| SI0929527T1 (en) | 2005-02-28 |
| WO1998013351A1 (fr) | 1998-04-02 |
| HUP9904161A2 (hu) | 2000-05-28 |
| AU711358B2 (en) | 1999-10-14 |
| CA2266357A1 (fr) | 1998-04-02 |
| ATE280761T1 (de) | 2004-11-15 |
| CA2266357C (fr) | 2003-07-29 |
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