SE468642B - Poly-4-aminopyrrol-2-karboxamidoderivat och foerfarande foer deras framstaellning och en farmaceutisk komposition - Google Patents
Poly-4-aminopyrrol-2-karboxamidoderivat och foerfarande foer deras framstaellning och en farmaceutisk kompositionInfo
- Publication number
- SE468642B SE468642B SE8603098A SE8603098A SE468642B SE 468642 B SE468642 B SE 468642B SE 8603098 A SE8603098 A SE 8603098A SE 8603098 A SE8603098 A SE 8603098A SE 468642 B SE468642 B SE 468642B
- Authority
- SE
- Sweden
- Prior art keywords
- methyl
- carboxamido
- pyrrole
- propyl
- dimethylamine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 26
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 7
- 229940053202 antiepileptics carboxamide derivative Drugs 0.000 title 1
- -1 methyloxiranyl Chemical group 0.000 claims description 179
- 150000001875 compounds Chemical class 0.000 claims description 132
- UPBAOYRENQEPJO-UHFFFAOYSA-N n-[5-[[5-[(3-amino-3-iminopropyl)carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-4-formamido-1-methylpyrrole-2-carboxamide Chemical compound CN1C=C(NC=O)C=C1C(=O)NC1=CN(C)C(C(=O)NC2=CN(C)C(C(=O)NCCC(N)=N)=C2)=C1 UPBAOYRENQEPJO-UHFFFAOYSA-N 0.000 claims description 53
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 claims description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 42
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical group 0.000 claims description 27
- 125000005518 carboxamido group Chemical group 0.000 claims description 21
- 108010042747 stallimycin Proteins 0.000 claims description 21
- 229950009902 stallimycin Drugs 0.000 claims description 20
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 13
- GNFWGDKKNWGGJY-UHFFFAOYSA-N propanimidamide Chemical compound CCC(N)=N GNFWGDKKNWGGJY-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 10
- 239000013543 active substance Substances 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000000466 oxiranyl group Chemical group 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004069 aziridinyl group Chemical group 0.000 claims description 4
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 4
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 125000004970 halomethyl group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 230000000840 anti-viral effect Effects 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- VKEYSDOZJDFCNS-UHFFFAOYSA-N n-[5-[3-(dimethylamino)propyl-methylcarbamoyl]-1h-pyrrol-3-yl]-n-methyl-4-(oxirane-2-carbonylamino)-1h-pyrrole-2-carboxamide Chemical compound N1C(C(=O)N(C)CCCN(C)C)=CC(N(C)C(=O)C=2NC=C(NC(=O)C3OC3)C=2)=C1 VKEYSDOZJDFCNS-UHFFFAOYSA-N 0.000 claims description 2
- FFTQGPPWDYKOBX-UHFFFAOYSA-N n-[5-[3-(dimethylamino)propyl-methylcarbamoyl]-1h-pyrrol-3-yl]-n-methyl-4-[(3-methyloxirane-2-carbonyl)amino]-1h-pyrrole-2-carboxamide Chemical compound CC1OC1C(=O)NC1=CNC(C(=O)N(C)C=2C=C(NC=2)C(=O)N(C)CCCN(C)C)=C1 FFTQGPPWDYKOBX-UHFFFAOYSA-N 0.000 claims description 2
- YRLJKQABNMEKGQ-UHFFFAOYSA-N n-[5-[3-(dimethylamino)propyl-methylcarbamoyl]-1h-pyrrol-3-yl]-n-methyl-4-[[methyl(nitroso)carbamoyl]amino]-1h-pyrrole-2-carboxamide Chemical compound N1C(C(=O)N(C)CCCN(C)C)=CC(N(C)C(=O)C=2NC=C(NC(=O)N(C)N=O)C=2)=C1 YRLJKQABNMEKGQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- JQDXZJYAUSVHDH-UHFFFAOYSA-N 3-chloropropanamide Chemical compound NC(=O)CCCl JQDXZJYAUSVHDH-UHFFFAOYSA-N 0.000 claims 1
- LPCVDKXLFFGSOS-UHFFFAOYSA-N 4-[[2-chloroethyl(nitroso)carbamoyl]amino]-N-[5-[3-(dimethylamino)propyl-methylcarbamoyl]-1H-pyrrol-3-yl]-N-methyl-1H-pyrrole-2-carboxamide Chemical compound CN(C(=O)C=1NC=C(C1)N(C(=O)C=1NC=C(C1)NC(=O)N(N=O)CCCl)C)CCCN(C)C LPCVDKXLFFGSOS-UHFFFAOYSA-N 0.000 claims 1
- 230000000259 anti-tumor effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- CZGLDFNFPHQLMW-UHFFFAOYSA-N n-[5-[(3-amino-3-iminopropyl)-methylcarbamoyl]-1h-pyrrol-3-yl]-4-[[2-chloroethyl(nitroso)carbamoyl]amino]-n-methyl-1h-pyrrole-2-carboxamide Chemical compound N1C(C(=O)N(CCC(N)=N)C)=CC(N(C)C(=O)C=2NC=C(NC(=O)N(CCCl)N=O)C=2)=C1 CZGLDFNFPHQLMW-UHFFFAOYSA-N 0.000 claims 1
- KXUZOSQRTBETNJ-UHFFFAOYSA-N n-[5-[(3-amino-3-iminopropyl)-methylcarbamoyl]-1h-pyrrol-3-yl]-n-methyl-4-[(3-methyloxirane-2-carbonyl)amino]-1h-pyrrole-2-carboxamide Chemical compound CC1OC1C(=O)NC1=CNC(C(=O)N(C)C=2C=C(NC=2)C(=O)N(C)CCC(N)=N)=C1 KXUZOSQRTBETNJ-UHFFFAOYSA-N 0.000 claims 1
- 238000005192 partition Methods 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- PRAHCKGOTFKWKD-UHFFFAOYSA-N dimethyl(propyl)azanium;chloride Chemical compound Cl.CCCN(C)C PRAHCKGOTFKWKD-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- DFWRZHZPJJAJMX-UHFFFAOYSA-N propanimidamide;hydrochloride Chemical compound Cl.CCC(N)=N DFWRZHZPJJAJMX-UHFFFAOYSA-N 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 210000004027 cell Anatomy 0.000 description 12
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- SFYSJFJQEGCACQ-UHFFFAOYSA-N n-[5-[[5-[(3-amino-3-iminopropyl)carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-4-formamido-1-methylpyrrole-2-carboxamide;hydron;chloride Chemical compound [Cl-].CN1C=C(NC=O)C=C1C(=O)NC1=CN(C)C(C(=O)NC2=CN(C)C(C(=O)NCCC([NH3+])=N)=C2)=C1 SFYSJFJQEGCACQ-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
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- 239000003054 catalyst Substances 0.000 description 6
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 5
- VBXZSFNZVNDOPB-UHFFFAOYSA-N 1,4,5,6-tetrahydropyrimidine Chemical compound C1CNC=NC1 VBXZSFNZVNDOPB-UHFFFAOYSA-N 0.000 description 5
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- 230000000694 effects Effects 0.000 description 5
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
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- 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)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polyamides (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB858517922A GB8517922D0 (en) | 1985-07-16 | 1985-07-16 | Carboxamido derivatives |
| GB868613594A GB8613594D0 (en) | 1986-06-04 | 1986-06-04 | Poly-4-aminopyrrole-2-carboxamido derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8603098D0 SE8603098D0 (sv) | 1986-07-11 |
| SE8603098L SE8603098L (sv) | 1987-01-17 |
| SE468642B true SE468642B (sv) | 1993-02-22 |
Family
ID=26289538
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8603098A SE468642B (sv) | 1985-07-16 | 1986-07-11 | Poly-4-aminopyrrol-2-karboxamidoderivat och foerfarande foer deras framstaellning och en farmaceutisk komposition |
Country Status (26)
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN85103908A (zh) * | 1985-07-16 | 1986-11-05 | 法米塔利·卡洛·埃尔巴有限公司 | 制备4′-表多克索红菌素的新方法 |
| GB8906709D0 (en) * | 1989-03-23 | 1989-05-10 | Creighton Andrew M | Acryloyl substituted pyrrole derivatives |
| IT1243389B (it) * | 1990-11-22 | 1994-06-10 | Menarini Farma Ind | Derivati poliaminopirrolcarbossiamidici, processi di preparazione e composizioni farmaceutiche che li contengono. |
| CA2103665C (en) * | 1991-02-06 | 2003-04-15 | J. William Lown | Oligopeptide antiretroviral agents |
| IT1247878B (it) * | 1991-02-15 | 1995-01-05 | Menarini Farma Ind | Derivati poli-4-aminopirrol-2-carbossiamidici,processi di preparazione e composizioni farmaceutiche che li contengono |
| GB2260134A (en) * | 1991-10-04 | 1993-04-07 | Erba Carlo Spa | Derivatives of poly-5-amino-3-carboxy-1-methyl compounds |
| IT1262921B (it) * | 1992-01-10 | 1996-07-22 | Federico Arcamone | Agenti antitumorali analoghi di oligopeptidi pirrol-amidinici retroversi processi di preparazione e prodotti farmaceutici che li contengono |
| GB9416005D0 (en) * | 1994-08-08 | 1994-09-28 | Erba Carlo Spa | Peptidic compounds analogous to distamycin a and process for their preparation |
| US5717110A (en) * | 1995-09-12 | 1998-02-10 | Kyowa Hakko Kogyo Co., Ltd. | UCH15 compounds |
| EP0880499A1 (en) * | 1996-02-02 | 1998-12-02 | PHARMACIA & UPJOHN S.p.A. | Distamycin derivatives, process for preparing them, and their use as antitumor and antiviral agents |
| GB9615692D0 (en) * | 1996-07-25 | 1996-09-04 | Pharmacia Spa | Acryloyl substituted distamycin derivatives, process for preparing them, and their use as antitumor and antiviral agents |
| GB0011059D0 (en) | 2000-05-08 | 2000-06-28 | Pharmacia & Upjohn Spa | Use of substituted acryloyl distamycin derivatives in the treatment of tumours associated with high levels of glutathione |
| GB0015446D0 (en) | 2000-06-23 | 2000-08-16 | Pharmacia & Upjohn Spa | Combined therapy against tumors comprising substituted acryloyl distamycin derivates,taxanes and/or antimetabolites |
| GB0015447D0 (en) | 2000-06-23 | 2000-08-16 | Pharmacia & Upjohn Spa | Combined therapy against tumors comprising substituted acryloyl derivates and alkylating agents |
| GB0016447D0 (en) | 2000-07-04 | 2000-08-23 | Pharmacia & Upjohn Spa | Process for preparing distamycin derivatives |
| US6969592B2 (en) | 2001-09-26 | 2005-11-29 | Pharmacia Italia S.P.A. | Method for predicting the sensitivity to chemotherapy |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR86210E (enrdf_load_stackoverflow) * | 1963-04-04 | 1966-03-23 | ||
| BR6461040D0 (pt) * | 1963-07-26 | 1973-08-02 | Farmaceutici Italia | Processo para preparar novos derivados de pirrol |
| DE1795539A1 (de) * | 1963-07-26 | 1972-01-13 | Farmaceutici Italia | Verfahren zur Herstellung von neuen Pyrrolderivaten und ihren Salzen |
| BE666612A (enrdf_load_stackoverflow) * | 1963-07-26 | 1965-11-03 | ||
| NL130086C (enrdf_load_stackoverflow) * | 1964-07-14 | 1970-06-15 | ||
| CN85103908A (zh) * | 1985-07-16 | 1986-11-05 | 法米塔利·卡洛·埃尔巴有限公司 | 制备4′-表多克索红菌素的新方法 |
-
1986
- 1986-07-11 AT AT0188886A patent/AT387013B/de not_active IP Right Cessation
- 1986-07-11 SE SE8603098A patent/SE468642B/sv not_active IP Right Cessation
- 1986-07-14 IL IL79402A patent/IL79402A/xx not_active IP Right Cessation
- 1986-07-14 IE IE187586A patent/IE59073B1/en not_active IP Right Cessation
- 1986-07-14 AU AU60202/86A patent/AU587841B2/en not_active Ceased
- 1986-07-14 NL NL8601837A patent/NL8601837A/xx not_active Application Discontinuation
- 1986-07-14 HU HU862904A patent/HU205949B/hu not_active IP Right Cessation
- 1986-07-14 ES ES8600290A patent/ES2000502A6/es not_active Expired
- 1986-07-14 NZ NZ216829A patent/NZ216829A/xx unknown
- 1986-07-15 JP JP61164879A patent/JPH0780843B2/ja not_active Expired - Lifetime
- 1986-07-15 KR KR1019860005715A patent/KR930010496B1/ko not_active Expired - Fee Related
- 1986-07-15 IT IT21125/86A patent/IT1196488B/it active
- 1986-07-15 FR FR868610294A patent/FR2585018B1/fr not_active Expired
- 1986-07-15 DK DK335986A patent/DK335986A/da not_active Application Discontinuation
- 1986-07-15 CA CA000513760A patent/CA1285934C/en not_active Expired - Lifetime
- 1986-07-15 CH CH2820/86A patent/CH674206A5/de not_active IP Right Cessation
- 1986-07-15 BE BE0/216924A patent/BE905110A/fr not_active IP Right Cessation
- 1986-07-15 DE DE3623880A patent/DE3623880A1/de not_active Withdrawn
- 1986-07-15 PH PH34014A patent/PH24714A/en unknown
- 1986-07-15 GR GR861841A patent/GR861841B/el unknown
- 1986-07-15 PT PT82984A patent/PT82984B/pt not_active IP Right Cessation
- 1986-07-15 NO NO862860A patent/NO168826C/no unknown
- 1986-07-16 FI FI862959A patent/FI83640C/fi not_active IP Right Cessation
- 1986-07-16 CN CN86104787A patent/CN1018825B/zh not_active Expired
- 1986-07-16 CS CS865412A patent/CS276981B6/cs unknown
- 1986-07-16 GB GB8617292A patent/GB2178036B/en not_active Expired
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