IL36398A - 3,4-dihydroisoquinoline derivatives,processes for their preparation and pharmaceutical compositions containing the same - Google Patents
3,4-dihydroisoquinoline derivatives,processes for their preparation and pharmaceutical compositions containing the sameInfo
- Publication number
- IL36398A IL36398A IL36398A IL3639871A IL36398A IL 36398 A IL36398 A IL 36398A IL 36398 A IL36398 A IL 36398A IL 3639871 A IL3639871 A IL 3639871A IL 36398 A IL36398 A IL 36398A
- Authority
- IL
- Israel
- Prior art keywords
- dihydroisoquinoline
- acid addition
- quaternary ammonium
- radical
- phenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 24
- NKSZCPBUWGZONP-UHFFFAOYSA-N 3,4-dihydroisoquinoline Chemical class C1=CC=C2C=NCCC2=C1 NKSZCPBUWGZONP-UHFFFAOYSA-N 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- -1 alkylene radical Chemical class 0.000 claims description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- VPKAHUMPZYVNIV-UHFFFAOYSA-N 1,4-dihydroisoquinoline Chemical class C1=CC=C2CC=NCC2=C1 VPKAHUMPZYVNIV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004807 2-methylethylene group Chemical group [H]C([H])([H])C([H])([*:2])C([H])([H])[*:1] 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000008016 pharmaceutical coating Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- JNFLSJUGIONDMJ-UHFFFAOYSA-N 2-n,2-n-diethylpropane-1,2-diamine Chemical compound CCN(CC)C(C)CN JNFLSJUGIONDMJ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 230000003226 decolorizating effect Effects 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- IOEPOEDBBPRAEI-UHFFFAOYSA-N 1,2-dihydroisoquinoline Chemical class C1=CC=C2CNC=CC2=C1 IOEPOEDBBPRAEI-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000008247 solid mixture Substances 0.000 description 3
- 239000001117 sulphuric acid Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- QJKLPACBLDYFMV-UHFFFAOYSA-N C1(=CC=CC=C1)C1CNC(C2=CC=CC=C12)=S Chemical compound C1(=CC=CC=C1)C1CNC(C2=CC=CC=C12)=S QJKLPACBLDYFMV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- SFNJUHMQHYRSJI-UHFFFAOYSA-N (1-isothiocyanato-2-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(N=C=S)CC1=CC=CC=C1 SFNJUHMQHYRSJI-UHFFFAOYSA-N 0.000 description 1
- HCMJWOGOISXSDL-UHFFFAOYSA-N (2-isothiocyanato-1-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(CN=C=S)C1=CC=CC=C1 HCMJWOGOISXSDL-UHFFFAOYSA-N 0.000 description 1
- XADXWWLTECVAAE-UHFFFAOYSA-N 1,1-diphenylethanamine Chemical compound C=1C=CC=CC=1C(N)(C)C1=CC=CC=C1 XADXWWLTECVAAE-UHFFFAOYSA-N 0.000 description 1
- XFSBVAOIAHNAPC-XTHSEXKGSA-N 16-Ethyl-1alpha,6alpha,19beta-trimethoxy-4-(methoxymethyl)-aconitane-3alpha,8,10alpha,11,18alpha-pentol, 8-acetate 10-benzoate Chemical compound O([C@H]1[C@]2(O)C[C@H]3[C@@]45C6[C@@H]([C@@]([C@H]31)(OC(C)=O)[C@@H](O)[C@@H]2OC)[C@H](OC)[C@@H]4[C@]([C@@H](C[C@@H]5OC)O)(COC)CN6CC)C(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-XTHSEXKGSA-N 0.000 description 1
- NMKWKTZCPBLCJI-UHFFFAOYSA-N 2,2-diphenylethanamine;hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(C[NH3+])C1=CC=CC=C1 NMKWKTZCPBLCJI-UHFFFAOYSA-N 0.000 description 1
- HSKBGALULOFBAM-UHFFFAOYSA-N 2,3-dihydroxy-4-methylidene-3h-naphthalene-1-carboxylic acid Chemical class C1=CC=C2C(=C)C(O)C(O)=C(C(O)=O)C2=C1 HSKBGALULOFBAM-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LPMXVESGRSUGHW-UHFFFAOYSA-N Acolongiflorosid K Natural products OC1C(O)C(O)C(C)OC1OC1CC2(O)CCC3C4(O)CCC(C=5COC(=O)C=5)C4(C)CC(O)C3C2(CO)C(O)C1 LPMXVESGRSUGHW-UHFFFAOYSA-N 0.000 description 1
- XFSBVAOIAHNAPC-UHFFFAOYSA-N Aconitin Natural products CCN1CC(C(CC2OC)O)(COC)C3C(OC)C(C(C45)(OC(C)=O)C(O)C6OC)C1C32C4CC6(O)C5OC(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
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- 206010048610 Cardiotoxicity Diseases 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 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
- C07D217/22—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR707008932A FR2081572B1 (is") | 1970-03-12 | 1970-03-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL36398A0 IL36398A0 (en) | 1971-05-26 |
| IL36398A true IL36398A (en) | 1973-10-25 |
Family
ID=9052168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL36398A IL36398A (en) | 1970-03-12 | 1971-03-11 | 3,4-dihydroisoquinoline derivatives,processes for their preparation and pharmaceutical compositions containing the same |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3759924A (is") |
| JP (1) | JPS5341156B1 (is") |
| AT (1) | AT303042B (is") |
| BE (1) | BE764133A (is") |
| CA (1) | CA933928A (is") |
| CH (1) | CH521347A (is") |
| DE (1) | DE2112026C3 (is") |
| DK (1) | DK126000B (is") |
| ES (1) | ES389180A1 (is") |
| FI (1) | FI49034C (is") |
| FR (1) | FR2081572B1 (is") |
| GB (1) | GB1285016A (is") |
| IE (1) | IE35209B1 (is") |
| IL (1) | IL36398A (is") |
| NL (1) | NL7102897A (is") |
| NO (1) | NO133400C (is") |
| SE (1) | SE360655B (is") |
| ZA (1) | ZA711602B (is") |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61109470U (is") * | 1984-12-20 | 1986-07-11 | ||
| US6426415B1 (en) | 1997-09-03 | 2002-07-30 | Guilford Pharmaceuticals Inc. | Alkoxy-substituted compounds, methods and compositions for inhibiting parp activity |
| US20020028813A1 (en) * | 1997-09-03 | 2002-03-07 | Paul F. Jackson | Thioalkyl compounds, methods, and compositions for inhibiting parp activity |
| US6346536B1 (en) | 1997-09-03 | 2002-02-12 | Guilford Pharmaceuticals Inc. | Poly(ADP-ribose) polymerase inhibitors and method for treating neural or cardiovascular tissue damage using the same |
| US6197785B1 (en) | 1997-09-03 | 2001-03-06 | Guilford Pharmaceuticals Inc. | Alkoxy-substituted compounds, methods, and compositions for inhibiting PARP activity |
| US6635642B1 (en) | 1997-09-03 | 2003-10-21 | Guilford Pharmaceuticals Inc. | PARP inhibitors, pharmaceutical compositions comprising same, and methods of using same |
| AU9298098A (en) * | 1997-09-03 | 1999-03-22 | Guilford Pharmaceuticals Inc. | Amino-substituted compounds, methods, and compositions for inhibiting parp activity |
| US6514983B1 (en) | 1997-09-03 | 2003-02-04 | Guilford Pharmaceuticals Inc. | Compounds, methods and pharmaceutical compositions for treating neural or cardiovascular tissue damage |
| US6291425B1 (en) * | 1999-09-01 | 2001-09-18 | Guilford Pharmaceuticals Inc. | Compounds, methods and pharmaceutical compositions for treating cellular damage, such as neural or cardiovascular tissue damage |
| US6395749B1 (en) | 1998-05-15 | 2002-05-28 | Guilford Pharmaceuticals Inc. | Carboxamide compounds, methods, and compositions for inhibiting PARP activity |
| US6387902B1 (en) | 1998-12-31 | 2002-05-14 | Guilford Pharmaceuticals, Inc. | Phenazine compounds, methods and pharmaceutical compositions for inhibiting PARP |
| US6723733B2 (en) | 2000-05-19 | 2004-04-20 | Guilford Pharmaceuticals, Inc. | Sulfonamide and carbamide derivatives of 6(5H)phenanthridinones and their uses |
| AU2001275085A1 (en) | 2000-06-01 | 2001-12-11 | Guilford Pharmaceuticals Inc. | Methods, compounds and compositions for treating gout |
| US6545011B2 (en) | 2000-07-13 | 2003-04-08 | Guilford Pharmaceuticals Inc. | Substituted 4,9-dihydrocyclopenta[imn]phenanthridine-5-ones, derivatives thereof and their uses |
| JP5627574B2 (ja) | 2008-06-03 | 2014-11-19 | インターミューン， インコーポレイテッド | 炎症性および線維性疾患を治療するための化合物および方法 |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| KR102373700B1 (ko) | 2014-04-02 | 2022-03-11 | 인터뮨, 인크. | 항섬유성 피리디논 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3227085A (en) * | 1963-09-05 | 1966-01-04 | James L Ramer | Shot shell |
| DE1670694B2 (de) * | 1966-05-05 | 1976-07-22 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von tetrahydroisochinolinen |
| FR2028672A6 (is") * | 1968-03-06 | 1970-10-16 | Rhone Poulenc Sa | |
| FR1583755A (is") * | 1968-03-06 | 1969-12-05 | ||
| GB1244501A (en) * | 1968-03-09 | 1971-09-02 | Aspro Nicholas Ltd | Heterocyclic amines |
-
1970
- 1970-03-12 FR FR707008932A patent/FR2081572B1/fr not_active Expired
-
1971
- 1971-02-12 FI FI710404A patent/FI49034C/fi active
- 1971-03-04 NL NL7102897A patent/NL7102897A/xx not_active Application Discontinuation
- 1971-03-11 IL IL36398A patent/IL36398A/en unknown
- 1971-03-11 ZA ZA711602A patent/ZA711602B/xx unknown
- 1971-03-11 SE SE03148/71A patent/SE360655B/xx unknown
- 1971-03-11 US US00123375A patent/US3759924A/en not_active Expired - Lifetime
- 1971-03-11 IE IE307/71A patent/IE35209B1/xx unknown
- 1971-03-11 CA CA107530A patent/CA933928A/en not_active Expired
- 1971-03-11 BE BE764133A patent/BE764133A/xx unknown
- 1971-03-11 DK DK116471AA patent/DK126000B/da unknown
- 1971-03-11 CH CH359771A patent/CH521347A/fr not_active IP Right Cessation
- 1971-03-11 JP JP1285971A patent/JPS5341156B1/ja active Pending
- 1971-03-11 NO NO925/71A patent/NO133400C/no unknown
- 1971-03-12 AT AT216171A patent/AT303042B/de not_active IP Right Cessation
- 1971-03-12 ES ES389180A patent/ES389180A1/es not_active Expired
- 1971-03-12 DE DE2112026A patent/DE2112026C3/de not_active Expired
- 1971-04-19 GB GB23784/71A patent/GB1285016A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IE35209L (en) | 1971-09-12 |
| FI49034B (is") | 1974-12-02 |
| CA933928A (en) | 1973-09-18 |
| GB1285016A (en) | 1972-08-09 |
| JPS5341156B1 (is") | 1978-10-31 |
| NO133400C (is") | 1976-04-28 |
| DE2112026C3 (de) | 1979-10-25 |
| DE2112026B2 (de) | 1979-03-08 |
| ZA711602B (en) | 1971-11-24 |
| FR2081572B1 (is") | 1973-04-06 |
| DE2112026A1 (de) | 1971-09-23 |
| SE360655B (is") | 1973-10-01 |
| US3759924A (en) | 1973-09-18 |
| IL36398A0 (en) | 1971-05-26 |
| NL7102897A (is") | 1971-09-14 |
| CH521347A (fr) | 1972-04-15 |
| DK126000B (da) | 1973-05-28 |
| ES389180A1 (es) | 1973-06-01 |
| IE35209B1 (en) | 1975-12-10 |
| FR2081572A1 (is") | 1971-12-10 |
| NO133400B (is") | 1976-01-19 |
| FI49034C (fi) | 1975-03-10 |
| AT303042B (de) | 1972-11-10 |
| BE764133A (fr) | 1971-09-13 |
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