DE2007345A1 - Neue substituierte Hexahydroimidazochinoline und deren Säureanlagerungssalze - Google Patents
Neue substituierte Hexahydroimidazochinoline und deren SäureanlagerungssalzeInfo
- Publication number
- DE2007345A1 DE2007345A1 DE19702007345 DE2007345A DE2007345A1 DE 2007345 A1 DE2007345 A1 DE 2007345A1 DE 19702007345 DE19702007345 DE 19702007345 DE 2007345 A DE2007345 A DE 2007345A DE 2007345 A1 DE2007345 A1 DE 2007345A1
- Authority
- DE
- Germany
- Prior art keywords
- nitro
- compounds
- compounds according
- methyl
- acid addition
- 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
Links
- 150000003839 salts Chemical class 0.000 title claims description 9
- 239000002253 acid Substances 0.000 title claims description 7
- RYHOOHBSBHEVOC-UHFFFAOYSA-N 2,3,3a,4,5,9b-hexahydro-1H-imidazo[4,5-h]quinoline Chemical class N1CNC2CCC=3C=CC=NC3C21 RYHOOHBSBHEVOC-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 150000001204 N-oxides Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- BXMXVVHSVHUOLL-UHFFFAOYSA-N C1NCC2N1C1=CC=CC=C1CC2 Chemical class C1NCC2N1C1=CC=CC=C1CC2 BXMXVVHSVHUOLL-UHFFFAOYSA-N 0.000 claims description 2
- 150000005215 alkyl ethers Chemical class 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- -1 2-isopropyl-7-methyl-8-nitro-1,2,3,3a, 4,5-hexahydroimidazo - [1,5-a] -quinoline Chemical compound 0.000 description 14
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 8
- XRDXINBBVUAHGQ-UHFFFAOYSA-N n-[(6-methyl-7-nitro-1,2,3,4-tetrahydroquinolin-2-yl)methyl]propan-2-amine Chemical compound CC1=C([N+]([O-])=O)C=C2NC(CNC(C)C)CCC2=C1 XRDXINBBVUAHGQ-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 201000004409 schistosomiasis Diseases 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 210000001758 mesenteric vein Anatomy 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- XCGYUJZMCCFSRP-UHFFFAOYSA-N oxamniquine Chemical compound OCC1=C([N+]([O-])=O)C=C2NC(CNC(C)C)CCC2=C1 XCGYUJZMCCFSRP-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 210000003240 portal vein Anatomy 0.000 description 2
- 230000036515 potency Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- GZPUPQJMZKIVII-UHFFFAOYSA-N 3,4-dihydro-2h-quinolin-1-ylmethanamine Chemical class C1=CC=C2N(CN)CCCC2=C1 GZPUPQJMZKIVII-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- RHKWIGHJGOEUSM-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinoline Chemical group C1=CN=C2C(N=CN3)=C3C=CC2=C1 RHKWIGHJGOEUSM-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 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
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000242680 Schistosoma mansoni Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-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
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- LZXOBCACSWDKFB-UHFFFAOYSA-N n-[[6-(ethoxymethyl)-7-nitro-1,2,3,4-tetrahydroquinolin-2-yl]methyl]propan-2-amine Chemical compound C1CC(CNC(C)C)NC2=C1C=C(COCC)C([N+]([O-])=O)=C2 LZXOBCACSWDKFB-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 238000010992 reflux Methods 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
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 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
- 150000003530 tetrahydroquinolines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8882/69A GB1278272A (en) | 1969-02-19 | 1969-02-19 | Substituted hexahydro-imidazoquinolines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2007345A1 true DE2007345A1 (de) | 1970-09-17 |
Family
ID=9861114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702007345 Pending DE2007345A1 (de) | 1969-02-19 | 1970-02-18 | Neue substituierte Hexahydroimidazochinoline und deren Säureanlagerungssalze |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3668208A (enExample) |
| JP (1) | JPS5016796B1 (enExample) |
| CH (1) | CH521979A (enExample) |
| DE (1) | DE2007345A1 (enExample) |
| FR (1) | FR2034556B1 (enExample) |
| GB (1) | GB1278272A (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1347493A (en) * | 1971-02-11 | 1974-02-27 | Aspro Nicholas Ltd | Benzazine derivatives |
| US3917610A (en) * | 1972-06-30 | 1975-11-04 | Chinoin Gyogyszer Es Vegyeszet | Amino-imidazo and amino-pyrazolo-isoquinolines and process for the preparation thereof |
| US3901897A (en) * | 1972-10-05 | 1975-08-26 | Squibb & Sons Inc | 1,2,3,4,4a,5,6,7-octahydro-7-aryl-isoquinolines and derivatives thereof |
| JPS5227199U (enExample) * | 1975-08-19 | 1977-02-25 | ||
| US4141898A (en) * | 1976-08-06 | 1979-02-27 | Pfizer Inc. | Imidazo pyridinium quaternary salts as hypoglycemic agents |
| US4075343A (en) * | 1976-09-13 | 1978-02-21 | Pfizer Inc. | Anti-allergenic 5-alkoxyimidazo[1,2-A]quinoline-2-carboxylic acids and derivatives thereof |
| FR2624861B1 (fr) * | 1987-12-21 | 1990-06-01 | Delalande Sa | Carbamates tricycliques, leur procede de preparation et leur application en therapeutique |
| USRE35840E (en) * | 1993-11-19 | 1998-07-07 | Pharmacia & Upjohn Company | Imidazo 1,5-a!quinolines for treatment of anxiety and sleep disorders |
| AU722043B2 (en) * | 1997-01-24 | 2000-07-20 | Synqor, Inc. | High efficiency power converter |
| CN117700413A (zh) * | 2024-02-05 | 2024-03-15 | 湖南工程学院 | 一种六氢咪唑并[2,1-a]异喹啉衍生物及其合成方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1166538A (en) | 1967-06-10 | 1969-10-08 | Pfizer Ltd | Substituted Tetrahydroquinolines |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3329620A (en) * | 1963-04-01 | 1967-07-04 | Hooker Chemical Corp | Novel phosphorus sulfide product and method for its manufacture |
| GB1011311A (en) * | 1963-07-04 | 1965-11-24 | Parke Davis & Co | Antiparasitic compositions and use thereof |
| GB1050901A (enExample) * | 1964-02-06 | |||
| US3454579A (en) * | 1967-08-17 | 1969-07-08 | American Cyanamid Co | Imidazo(1,5-a)quinolin-1-one and thione derivatives |
| US3565902A (en) * | 1967-09-15 | 1971-02-23 | American Cyanamid Co | 1,2-dihydro-3h-imidazo(1,5-a)indol-3-ones and 3-thiones |
| US3557120A (en) * | 1969-05-21 | 1971-01-19 | Sterling Drug Inc | Hexahydroimidazoisoquinolines |
-
1969
- 1969-02-19 GB GB8882/69A patent/GB1278272A/en not_active Expired
-
1970
- 1970-02-13 US US11308A patent/US3668208A/en not_active Expired - Lifetime
- 1970-02-18 DE DE19702007345 patent/DE2007345A1/de active Pending
- 1970-02-19 CH CH237570A patent/CH521979A/fr not_active IP Right Cessation
- 1970-02-19 JP JP45014502A patent/JPS5016796B1/ja active Pending
- 1970-02-19 FR FR7006010A patent/FR2034556B1/fr not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1166538A (en) | 1967-06-10 | 1969-10-08 | Pfizer Ltd | Substituted Tetrahydroquinolines |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2034556B1 (enExample) | 1974-04-12 |
| JPS5016796B1 (enExample) | 1975-06-16 |
| CH521979A (fr) | 1972-04-30 |
| US3668208A (en) | 1972-06-06 |
| FR2034556A1 (enExample) | 1970-12-11 |
| GB1278272A (en) | 1972-06-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHW | Rejection |