JPS5931514B2 - ４，５，６，７−テトラヒドロ−チエノ〔３，２−ｃ〕ピリジン誘導体およびその製造方法 - Google Patents
４，５，６，７−テトラヒドロ−チエノ〔３，２−ｃ〕ピリジン誘導体およびその製造方法Info
- Publication number
- JPS5931514B2 JPS5931514B2 JP51062176A JP6217676A JPS5931514B2 JP S5931514 B2 JPS5931514 B2 JP S5931514B2 JP 51062176 A JP51062176 A JP 51062176A JP 6217676 A JP6217676 A JP 6217676A JP S5931514 B2 JPS5931514 B2 JP S5931514B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- alkyl group
- carbon atoms
- compound
- hydrogen atom
- 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.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- OGUWOLDNYOTRBO-UHFFFAOYSA-N 4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical class C1NCCC2=C1C=CS2 OGUWOLDNYOTRBO-UHFFFAOYSA-N 0.000 title claims 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000012736 aqueous medium Substances 0.000 claims description 4
- 150000002466 imines Chemical class 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
- 239000002609 medium Substances 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 24
- 238000000921 elemental analysis Methods 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 108010058846 Ovalbumin Proteins 0.000 description 3
- 229940113118 carrageenan Drugs 0.000 description 3
- 235000010418 carrageenan Nutrition 0.000 description 3
- 229920001525 carrageenan Polymers 0.000 description 3
- 239000000679 carrageenan Substances 0.000 description 3
- 229940092253 ovalbumin Drugs 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 3
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000001760 anti-analgesic effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003756 stirring Methods 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
- FLXIOVQXMOFJRX-UHFFFAOYSA-N 2-methoxy-2-thiophen-2-ylethanamine Chemical compound COC(CN)C1=CC=CS1 FLXIOVQXMOFJRX-UHFFFAOYSA-N 0.000 description 1
- DLQPNVDFMLUZGW-UHFFFAOYSA-N 7-(2-methylpropoxy)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound CC(C)COC1CNCC2=C1SC=C2 DLQPNVDFMLUZGW-UHFFFAOYSA-N 0.000 description 1
- GFGXHMRVMINRSP-UHFFFAOYSA-N 7-ethoxy-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound CCOC1CNCC2=C1SC=C2 GFGXHMRVMINRSP-UHFFFAOYSA-N 0.000 description 1
- MVGITHRUGFIMHI-UHFFFAOYSA-N 7-ethoxy-6-methyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound CCOC1C(C)NCC2=C1SC=C2 MVGITHRUGFIMHI-UHFFFAOYSA-N 0.000 description 1
- PYDWKZUUVRRLGE-UHFFFAOYSA-N 7-methoxy-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound COC1CNCC2=C1SC=C2 PYDWKZUUVRRLGE-UHFFFAOYSA-N 0.000 description 1
- LGBOATCUAWXIEL-UHFFFAOYSA-N 7-methoxy-6-phenyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound N1CC=2C=CSC=2C(OC)C1C1=CC=CC=C1 LGBOATCUAWXIEL-UHFFFAOYSA-N 0.000 description 1
- TWIDNPLVBLPFNK-UHFFFAOYSA-N 7-phenylmethoxy-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1NCC=2C=CSC=2C1OCC1=CC=CC=C1 TWIDNPLVBLPFNK-UHFFFAOYSA-N 0.000 description 1
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 1
- 241000531434 Lamprocapnos spectabilis Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960003699 evans blue Drugs 0.000 description 1
- -1 for example Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 244000144993 groups of animals Species 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 210000001872 metatarsal bone Anatomy 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- MKYRMMMSZSVIGD-UHFFFAOYSA-N thieno[3,2-c]pyridine Chemical class N1=CC=C2SC=CC2=C1 MKYRMMMSZSVIGD-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7516635A FR2312246A1 (fr) | 1975-05-28 | 1975-05-28 | Derives de la tetrahydro-4,5,6,7 thieno (3,2-c) pyridine, leur procede de preparation et leurs applications |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS52294A JPS52294A (en) | 1977-01-05 |
| JPS5931514B2 true JPS5931514B2 (ja) | 1984-08-02 |
Family
ID=9155775
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51062176A Expired JPS5931514B2 (ja) | 1975-05-28 | 1976-05-28 | ４，５，６，７−テトラヒドロ−チエノ〔３，２−ｃ〕ピリジン誘導体およびその製造方法 |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4065460A (OSRAM) |
| JP (1) | JPS5931514B2 (OSRAM) |
| AR (1) | AR209360A1 (OSRAM) |
| AT (1) | AT347949B (OSRAM) |
| BE (1) | BE842249A (OSRAM) |
| CA (1) | CA1071632A (OSRAM) |
| CH (1) | CH596215A5 (OSRAM) |
| DD (1) | DD125215A5 (OSRAM) |
| DE (1) | DE2623566A1 (OSRAM) |
| DK (1) | DK227476A (OSRAM) |
| ES (1) | ES447495A1 (OSRAM) |
| FR (1) | FR2312246A1 (OSRAM) |
| GB (1) | GB1490050A (OSRAM) |
| GR (1) | GR59796B (OSRAM) |
| HU (1) | HU172175B (OSRAM) |
| IE (1) | IE42672B1 (OSRAM) |
| IL (1) | IL49368A0 (OSRAM) |
| LU (1) | LU74573A1 (OSRAM) |
| MX (1) | MX3212E (OSRAM) |
| NL (1) | NL180564C (OSRAM) |
| PH (1) | PH12026A (OSRAM) |
| PL (1) | PL97384B1 (OSRAM) |
| PT (1) | PT65040B (OSRAM) |
| RO (1) | RO69113A (OSRAM) |
| SE (1) | SE421622B (OSRAM) |
| SU (1) | SU604495A3 (OSRAM) |
| YU (1) | YU39612B (OSRAM) |
| ZA (1) | ZA762092B (OSRAM) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4163852A (en) * | 1975-07-09 | 1979-08-07 | Parcor | Process for the preparation of tetrahydro-thieno[3,2-c]- and [2,3-c]pyridine derivatives |
| FR2376860A1 (fr) * | 1977-01-07 | 1978-08-04 | Parcor | Tetrahydro-4,5,6,7 thieno (2,3-c) et (3,2-c) pyridines, leur procede de preparation et leur application therapeutique |
| FR2397417A1 (fr) * | 1977-07-12 | 1979-02-09 | Parcor | Procede de preparation de derives de la thienopyridine |
| US4419803A (en) * | 1981-02-04 | 1983-12-13 | Ashcombe Products Company | Method of forming a tool assembly |
| CA2682377A1 (en) * | 2007-03-30 | 2008-10-09 | Nippon Shinyaku Co., Ltd. | Heteroaryl derivatives |
| DE102011053619A1 (de) | 2011-09-14 | 2013-03-14 | Becker Marine Systems Gmbh & Co. Kg | Propellerdüse für Wasserfahrzeuge |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2215948B1 (OSRAM) * | 1973-02-01 | 1976-05-14 | Centre Etd Ind Pharma |
-
1975
- 1975-05-28 FR FR7516635A patent/FR2312246A1/fr active Granted
-
1976
- 1976-03-15 CH CH316276A patent/CH596215A5/xx not_active IP Right Cessation
- 1976-03-16 LU LU74573A patent/LU74573A1/xx unknown
- 1976-03-23 GR GR50383A patent/GR59796B/el unknown
- 1976-04-05 YU YU855/76A patent/YU39612B/xx unknown
- 1976-04-06 IE IE715/76A patent/IE42672B1/en unknown
- 1976-04-06 US US05/674,734 patent/US4065460A/en not_active Expired - Lifetime
- 1976-04-07 ZA ZA762092A patent/ZA762092B/xx unknown
- 1976-04-07 IL IL49368A patent/IL49368A0/xx unknown
- 1976-04-08 CA CA249,883A patent/CA1071632A/en not_active Expired
- 1976-04-27 PT PT65040A patent/PT65040B/pt unknown
- 1976-04-30 ES ES447495A patent/ES447495A1/es not_active Expired
- 1976-05-05 AR AR263207A patent/AR209360A1/es active
- 1976-05-06 NL NLAANVRAGE7604867,A patent/NL180564C/xx not_active IP Right Cessation
- 1976-05-10 SU SU762352255A patent/SU604495A3/ru active
- 1976-05-13 MX MX000232U patent/MX3212E/es unknown
- 1976-05-21 DK DK227476A patent/DK227476A/da unknown
- 1976-05-22 RO RO7686178A patent/RO69113A/ro unknown
- 1976-05-25 AT AT382076A patent/AT347949B/de not_active IP Right Cessation
- 1976-05-25 SE SE7605899A patent/SE421622B/xx not_active IP Right Cessation
- 1976-05-26 BE BE167354A patent/BE842249A/xx not_active IP Right Cessation
- 1976-05-26 DE DE19762623566 patent/DE2623566A1/de not_active Withdrawn
- 1976-05-27 GB GB22087/76A patent/GB1490050A/en not_active Expired
- 1976-05-27 PL PL1976189899A patent/PL97384B1/pl unknown
- 1976-05-27 PH PH18481A patent/PH12026A/en unknown
- 1976-05-28 JP JP51062176A patent/JPS5931514B2/ja not_active Expired
- 1976-05-28 HU HU76PA00001247A patent/HU172175B/hu not_active IP Right Cessation
- 1976-05-28 DD DD193079A patent/DD125215A5/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT347949B (de) | 1979-01-25 |
| CH596215A5 (OSRAM) | 1978-03-15 |
| ES447495A1 (es) | 1977-07-01 |
| YU39612B (en) | 1985-03-20 |
| DD125215A5 (OSRAM) | 1977-04-06 |
| PL97384B1 (pl) | 1978-02-28 |
| IL49368A0 (en) | 1976-06-30 |
| DK227476A (da) | 1976-11-29 |
| GR59796B (en) | 1978-02-28 |
| SE421622B (sv) | 1982-01-18 |
| ZA762092B (en) | 1977-04-27 |
| LU74573A1 (OSRAM) | 1976-09-01 |
| YU85576A (en) | 1982-05-31 |
| FR2312246B1 (OSRAM) | 1978-08-11 |
| BE842249A (fr) | 1976-11-26 |
| GB1490050A (en) | 1977-10-26 |
| PH12026A (en) | 1978-10-16 |
| FR2312246A1 (fr) | 1976-12-24 |
| HU172175B (hu) | 1978-06-28 |
| IE42672B1 (en) | 1980-09-24 |
| AR209360A1 (es) | 1977-04-15 |
| US4065460A (en) | 1977-12-27 |
| NL180564B (nl) | 1986-10-16 |
| JPS52294A (en) | 1977-01-05 |
| NL180564C (nl) | 1987-03-16 |
| PT65040A (fr) | 1976-05-01 |
| AU1435876A (en) | 1977-12-01 |
| SE7605899L (sv) | 1976-11-29 |
| IE42672L (en) | 1976-11-28 |
| NL7604867A (nl) | 1976-11-30 |
| RO69113A (ro) | 1980-08-15 |
| PT65040B (fr) | 1977-09-12 |
| MX3212E (es) | 1980-07-17 |
| SU604495A3 (ru) | 1978-04-25 |
| DE2623566A1 (de) | 1976-12-16 |
| CA1071632A (en) | 1980-02-12 |
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