JPS63150264A - 新規ベンゾ〔ｇ〕キノリン類 - Google Patents
新規ベンゾ〔ｇ〕キノリン類Info
- Publication number
- JPS63150264A JPS63150264A JP62294995A JP29499587A JPS63150264A JP S63150264 A JPS63150264 A JP S63150264A JP 62294995 A JP62294995 A JP 62294995A JP 29499587 A JP29499587 A JP 29499587A JP S63150264 A JPS63150264 A JP S63150264A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- free base
- addition salt
- acid addition
- compound
- 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
- RFQDDXWZZVRLKO-UHFFFAOYSA-N benzo[g]quinoline Chemical class N1=CC=CC2=CC3=CC=CC=C3C=C21 RFQDDXWZZVRLKO-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 66
- 239000002253 acid Substances 0.000 claims description 34
- 150000003839 salts Chemical group 0.000 claims description 28
- 239000012458 free base Substances 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- 230000003287 optical effect Effects 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000004202 carbamide Substances 0.000 claims description 8
- 230000028327 secretion Effects 0.000 claims description 7
- 102000003946 Prolactin Human genes 0.000 claims description 6
- 108010057464 Prolactin Proteins 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229940097325 prolactin Drugs 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000003291 dopaminomimetic effect Effects 0.000 claims description 3
- -1 hydroxy, methoxy Chemical group 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 239000008024 pharmaceutical diluent Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims 1
- 239000003136 dopamine receptor stimulating agent Substances 0.000 claims 1
- 229940005501 dopaminergic agent Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 description 3
- 229960002802 bromocriptine Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 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
- 201000000736 Amenorrhea Diseases 0.000 description 1
- 206010001928 Amenorrhoea Diseases 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 240000004183 Bongardia chrysogonum Species 0.000 description 1
- 102000015554 Dopamine receptor Human genes 0.000 description 1
- 108050004812 Dopamine receptor Proteins 0.000 description 1
- 208000001287 Galactorrhea Diseases 0.000 description 1
- 206010017600 Galactorrhoea Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- 238000007126 N-alkylation reaction Methods 0.000 description 1
- 206010036832 Prolactinoma Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 201000001880 Sexual dysfunction Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000000914 Solidago virgaurea Nutrition 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 231100000540 amenorrhea Toxicity 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000005661 deetherification reaction Methods 0.000 description 1
- 239000003405 delayed action preparation Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000006651 lactation Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000006193 liquid solution 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
- 231100000551 menstrual abnormality Toxicity 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 231100000872 sexual dysfunction Toxicity 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 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
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
-
- 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
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/08—Aza-anthracenes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3639855.1 | 1986-11-21 | ||
| DE3639855 | 1986-11-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63150264A true JPS63150264A (ja) | 1988-06-22 |
Family
ID=6314490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62294995A Pending JPS63150264A (ja) | 1986-11-21 | 1987-11-20 | 新規ベンゾ〔ｇ〕キノリン類 |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS63150264A (ko) |
| KR (1) | KR880006200A (ko) |
| AT (1) | AT393836B (ko) |
| AU (1) | AU604512B2 (ko) |
| BE (1) | BE1003219A3 (ko) |
| CH (1) | CH677668A5 (ko) |
| DK (1) | DK608787A (ko) |
| ES (1) | ES2011309A6 (ko) |
| FI (1) | FI875130A (ko) |
| FR (1) | FR2607134A1 (ko) |
| GB (1) | GB2198129B (ko) |
| GR (1) | GR871777B (ko) |
| HU (1) | HUT47914A (ko) |
| IL (1) | IL84538A (ko) |
| IT (1) | IT1211920B (ko) |
| LU (1) | LU87047A1 (ko) |
| NL (1) | NL8702680A (ko) |
| NZ (1) | NZ222612A (ko) |
| PH (1) | PH25125A (ko) |
| PT (1) | PT86178B (ko) |
| SE (1) | SE8704551L (ko) |
| ZA (1) | ZA878717B (ko) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1990000896A1 (en) * | 1988-07-22 | 1990-02-08 | Sandoz Ag | USE OF BENZO(g)QUINOLINES IN TREATMENT OF NICOTINE ADDICTION |
| TW357143B (en) * | 1995-07-07 | 1999-05-01 | Novartis Ag | Benzo[g]quinoline derivatives |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4526892A (en) * | 1981-03-03 | 1985-07-02 | Farmitalia Carlo Erba, S.P.A. | Dimethylaminoalkyl-3-(ergoline-8'βcarbonyl)-ureas |
| LU88619I2 (fr) * | 1981-10-16 | 1995-07-10 | Sandoz Ag | QUINAGOLIDE, éventuellement sous forme de sel, par exemple du chlorhydrate |
| GB8602372D0 (en) * | 1986-01-31 | 1986-03-05 | Sandoz Ltd | Organic compounds |
-
1987
- 1987-11-10 NL NL8702680A patent/NL8702680A/nl not_active Application Discontinuation
- 1987-11-12 CH CH4410/87A patent/CH677668A5/de not_active IP Right Cessation
- 1987-11-13 HU HU875063A patent/HUT47914A/hu unknown
- 1987-11-16 FR FR8715917A patent/FR2607134A1/fr not_active Withdrawn
- 1987-11-16 BE BE8701295A patent/BE1003219A3/fr not_active IP Right Cessation
- 1987-11-18 LU LU87047A patent/LU87047A1/fr unknown
- 1987-11-18 IT IT8748620A patent/IT1211920B/it active
- 1987-11-19 DK DK608787A patent/DK608787A/da not_active Application Discontinuation
- 1987-11-19 FI FI875130A patent/FI875130A/fi not_active IP Right Cessation
- 1987-11-19 SE SE8704551A patent/SE8704551L/xx not_active Application Discontinuation
- 1987-11-19 NZ NZ222612A patent/NZ222612A/xx unknown
- 1987-11-19 GB GB8727057A patent/GB2198129B/en not_active Expired - Lifetime
- 1987-11-19 PT PT86178A patent/PT86178B/pt not_active IP Right Cessation
- 1987-11-19 AU AU81409/87A patent/AU604512B2/en not_active Ceased
- 1987-11-19 IL IL84538A patent/IL84538A/xx unknown
- 1987-11-20 GR GR871777A patent/GR871777B/el unknown
- 1987-11-20 KR KR870013071A patent/KR880006200A/ko not_active Application Discontinuation
- 1987-11-20 ZA ZA878717A patent/ZA878717B/xx unknown
- 1987-11-20 JP JP62294995A patent/JPS63150264A/ja active Pending
- 1987-11-20 AT AT0306187A patent/AT393836B/de not_active IP Right Cessation
- 1987-11-20 ES ES8703316A patent/ES2011309A6/es not_active Expired - Lifetime
- 1987-11-20 PH PH36098A patent/PH25125A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI875130A0 (fi) | 1987-11-19 |
| NZ222612A (en) | 1991-07-26 |
| AT393836B (de) | 1991-12-27 |
| GB8727057D0 (en) | 1987-12-23 |
| PT86178B (pt) | 1990-11-07 |
| KR880006200A (ko) | 1988-07-22 |
| SE8704551L (sv) | 1988-05-22 |
| SE8704551D0 (sv) | 1987-11-19 |
| DK608787A (da) | 1988-05-22 |
| ES2011309A6 (es) | 1990-01-01 |
| HUT47914A (en) | 1989-04-28 |
| GB2198129B (en) | 1990-08-08 |
| NL8702680A (nl) | 1988-06-16 |
| LU87047A1 (fr) | 1988-06-13 |
| GB2198129A (en) | 1988-06-08 |
| IT1211920B (it) | 1989-11-08 |
| AU604512B2 (en) | 1990-12-20 |
| FI875130A (fi) | 1988-05-22 |
| IL84538A (en) | 1991-12-12 |
| ATA306187A (de) | 1991-06-15 |
| AU8140987A (en) | 1988-05-26 |
| BE1003219A3 (fr) | 1992-02-04 |
| CH677668A5 (ko) | 1991-06-14 |
| FR2607134A1 (fr) | 1988-05-27 |
| PT86178A (en) | 1987-12-01 |
| IL84538A0 (en) | 1988-04-29 |
| ZA878717B (en) | 1989-06-28 |
| IT8748620A0 (it) | 1987-11-18 |
| GR871777B (en) | 1988-03-24 |
| PH25125A (en) | 1991-02-19 |
| DK608787D0 (da) | 1987-11-19 |
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