SU1535378A3 - Способ получени гидрохлоридов производных дистамицина А - Google Patents
Способ получени гидрохлоридов производных дистамицина А Download PDFInfo
- Publication number
- SU1535378A3 SU1535378A3 SU864027842A SU4027842A SU1535378A3 SU 1535378 A3 SU1535378 A3 SU 1535378A3 SU 864027842 A SU864027842 A SU 864027842A SU 4027842 A SU4027842 A SU 4027842A SU 1535378 A3 SU1535378 A3 SU 1535378A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- halogen
- alkyl
- image
- group
- distamycin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 150000003840 hydrochlorides Chemical class 0.000 title claims 2
- VVNCNSJFMMFHPL-VKHMYHEASA-N D-penicillamine Chemical class CC(C)(S)[C@@H](N)C(O)=O VVNCNSJFMMFHPL-VKHMYHEASA-N 0.000 title 1
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 125000004069 aziridinyl group Chemical group 0.000 claims abstract description 6
- 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 class 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 abstract description 6
- 150000002367 halogens Chemical group 0.000 claims description 8
- 108010042747 stallimycin Proteins 0.000 claims description 2
- 229950009902 stallimycin Drugs 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 16
- -1 methyloxiranyl Chemical group 0.000 abstract description 7
- 125000000466 oxiranyl group Chemical group 0.000 abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 3
- 230000000840 anti-viral effect Effects 0.000 abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 3
- 239000001257 hydrogen Substances 0.000 abstract description 3
- 150000003839 salts Chemical class 0.000 abstract description 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002246 antineoplastic agent Substances 0.000 abstract 1
- 239000003443 antiviral agent Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 11
- 241000700605 Viruses Species 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- 230000003013 cytotoxicity Effects 0.000 description 4
- 231100000135 cytotoxicity Toxicity 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 206010039491 Sarcoma Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 230000010261 cell growth Effects 0.000 description 2
- 239000006285 cell suspension Substances 0.000 description 2
- 230000000120 cytopathologic effect Effects 0.000 description 2
- 230000001085 cytostatic effect Effects 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 208000032839 leukemia Diseases 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 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 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- 241000450599 DNA viruses Species 0.000 description 1
- 208000007093 Leukemia L1210 Diseases 0.000 description 1
- 241000725643 Respiratory syncytial virus Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 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 1
- 244000052769 pathogen Species 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 241000701161 unidentified adenovirus Species 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB858517923A GB8517923D0 (en) | 1985-07-16 | 1985-07-16 | Distamycin derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1535378A3 true SU1535378A3 (ru) | 1990-01-07 |
Family
ID=10582358
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU864027842A SU1535378A3 (ru) | 1985-07-16 | 1986-07-15 | Способ получени гидрохлоридов производных дистамицина А |
| SU874203631A SU1538893A3 (ru) | 1985-07-16 | 1987-11-11 | Способ получени гидрохлорида N-деформил-N [N,N -бис(2-хлорэтил)]дистамицина А |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU874203631A SU1538893A3 (ru) | 1985-07-16 | 1987-11-11 | Способ получени гидрохлорида N-деформил-N [N,N -бис(2-хлорэтил)]дистамицина А |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US4738980A (enExample) |
| JP (1) | JPH0780842B2 (enExample) |
| KR (1) | KR940003495B1 (enExample) |
| CN (2) | CN85103908A (enExample) |
| AT (1) | AT386822B (enExample) |
| AU (1) | AU584723B2 (enExample) |
| BE (1) | BE905109A (enExample) |
| CA (1) | CA1247627A (enExample) |
| CH (1) | CH671958A5 (enExample) |
| CZ (1) | CZ277823B6 (enExample) |
| DE (1) | DE3623853C2 (enExample) |
| DK (1) | DK335886A (enExample) |
| ES (1) | ES2000346A6 (enExample) |
| FI (1) | FI82929C (enExample) |
| FR (1) | FR2585019B1 (enExample) |
| GB (2) | GB8517923D0 (enExample) |
| GR (1) | GR861840B (enExample) |
| HU (1) | HU198087B (enExample) |
| IE (1) | IE59275B1 (enExample) |
| IL (1) | IL79401A (enExample) |
| IT (1) | IT1213103B (enExample) |
| NL (1) | NL8601838A (enExample) |
| NO (1) | NO169014C (enExample) |
| NZ (1) | NZ216828A (enExample) |
| PH (1) | PH23459A (enExample) |
| PT (1) | PT82985B (enExample) |
| SE (1) | SE468594B (enExample) |
| SU (2) | SU1535378A3 (enExample) |
| ZA (1) | ZA865262B (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE468642B (sv) * | 1985-07-16 | 1993-02-22 | Erba Farmitalia | Poly-4-aminopyrrol-2-karboxamidoderivat och foerfarande foer deras framstaellning och en farmaceutisk komposition |
| US5310752A (en) * | 1986-05-20 | 1994-05-10 | Farmitalia Carlo Erba Spa | Site specific alkylating agents |
| US5049579A (en) * | 1986-05-20 | 1991-09-17 | Farmitalia Carlo Erba, S.R.L. | Site specific alkylating agents |
| GB8612218D0 (en) * | 1986-05-20 | 1986-06-25 | Erba Farmitalia | Site specific alkylating agents |
| GB8906709D0 (en) * | 1989-03-23 | 1989-05-10 | Creighton Andrew M | Acryloyl substituted pyrrole derivatives |
| AU1224392A (en) * | 1991-02-06 | 1992-09-07 | Synphar Laboratories, Inc. | Oligopeptide antiretroviral agents |
| 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 |
| DE4205948C2 (de) * | 1992-02-24 | 1996-10-31 | Mannesmann Ag | Farbbandkassette für ein endloses Farbband |
| US5273991A (en) * | 1992-07-29 | 1993-12-28 | Research Corporation Technologies, Inc. | Imidazole-containing compositions and methods of use thereof analogs of distamycin |
| US5629348A (en) * | 1994-11-14 | 1997-05-13 | Nzym, Inc. | Methods and compositions for treating septoria infections |
| US5637621A (en) * | 1994-11-14 | 1997-06-10 | Nzym, Inc. | Methods and compositions for treating Botrytis infections |
| WO1996015104A2 (en) * | 1994-11-14 | 1996-05-23 | Nzym, Inc. | Methods and compositions for treating phytopathogenic fungi infections |
| DE19805431A1 (de) * | 1998-02-11 | 1999-08-12 | Merck Patent Gmbh | Heteroaromatische Oligoamide als Affinitätsliganden |
| US7078536B2 (en) * | 2001-03-14 | 2006-07-18 | Genesoft Pharmaceuticals, Inc. | Charged compounds comprising a nucleic acid binding moiety and uses therefor |
| CN1427839A (zh) * | 2000-03-16 | 2003-07-02 | 根索福特股份有限公司 | 含有核酸结合部分的带电荷化合物及其用途 |
| GB0015447D0 (en) * | 2000-06-23 | 2000-08-16 | Pharmacia & Upjohn Spa | Combined therapy against tumors comprising substituted acryloyl derivates and alkylating agents |
| ITTO20010633A1 (it) * | 2001-07-02 | 2003-01-02 | Univ Ferrara | Nuovo impiego di poliammidi eterocicliche e benzoeterocicliche strutturalmente correlate all'antibiotico naturale distamicina a. |
| EP1539151B1 (en) | 2002-08-02 | 2009-03-18 | Genesoft Pharmaceuticals, Inc. | Biaryl compounds having anti-infective activity |
| WO2004039318A2 (en) * | 2002-10-25 | 2004-05-13 | Genesoft Pharmaceuticals, Inc. | Anti-infective biaryl compounds |
| CA2508769A1 (en) * | 2002-12-10 | 2004-06-24 | Oscient Pharmaceuticals Corporation | Antibacterial compounds having a (pyrrole carboxamide)-(benzamide)-(imidazole carboxamide) motif |
| WO2005051318A2 (en) * | 2003-11-24 | 2005-06-09 | Viropharma Incorporated | Compounds, compositions and methods for treatment and prophylaxis of hepatitis c viral infections and associated diseases |
| WO2016159092A1 (ja) * | 2015-03-30 | 2016-10-06 | Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 | エピルビシンの製造方法およびその新規な製造中間体 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA557568A (en) * | 1958-05-20 | J. Weiss Martin | Substituted aminopyrrolecarboxylic acids and esters | |
| CA547128A (en) * | 1957-10-08 | W. Waller Coy | Substituted pyrrolecarboxamidopyrroles | |
| FR86210E (enExample) * | 1963-04-04 | 1966-03-23 | ||
| FR141F (enExample) * | 1963-07-26 | |||
| BR6461040D0 (pt) * | 1963-07-26 | 1973-08-02 | Farmaceutici Italia | Processo para preparar novos derivados de pirrol |
| BE666612A (enExample) * | 1963-07-26 | 1965-11-03 | ||
| DE1795539A1 (de) * | 1963-07-26 | 1972-01-13 | Farmaceutici Italia | Verfahren zur Herstellung von neuen Pyrrolderivaten und ihren Salzen |
| NL130086C (enExample) * | 1964-07-14 | 1970-06-15 | ||
| SE468642B (sv) * | 1985-07-16 | 1993-02-22 | Erba Farmitalia | Poly-4-aminopyrrol-2-karboxamidoderivat och foerfarande foer deras framstaellning och en farmaceutisk komposition |
| GB8612218D0 (en) * | 1986-05-20 | 1986-06-25 | Erba Farmitalia | Site specific alkylating agents |
-
1985
- 1985-06-08 CN CN198585103908A patent/CN85103908A/zh active Pending
- 1985-07-16 GB GB858517923A patent/GB8517923D0/en active Pending
- 1985-10-03 US US06/783,508 patent/US4738980A/en not_active Expired - Fee Related
-
1986
- 1986-07-11 SE SE8603099A patent/SE468594B/sv not_active IP Right Cessation
- 1986-07-11 AT AT0188786A patent/AT386822B/de not_active IP Right Cessation
- 1986-07-14 ES ES8600291A patent/ES2000346A6/es not_active Expired
- 1986-07-14 HU HU862903A patent/HU198087B/hu not_active IP Right Cessation
- 1986-07-14 IL IL79401A patent/IL79401A/xx not_active IP Right Cessation
- 1986-07-14 IE IE187486A patent/IE59275B1/en not_active IP Right Cessation
- 1986-07-14 NL NL8601838A patent/NL8601838A/xx not_active Application Discontinuation
- 1986-07-14 NZ NZ216828A patent/NZ216828A/xx unknown
- 1986-07-14 AU AU60203/86A patent/AU584723B2/en not_active Ceased
- 1986-07-15 PT PT82985A patent/PT82985B/pt not_active IP Right Cessation
- 1986-07-15 GR GR861840A patent/GR861840B/el unknown
- 1986-07-15 NO NO862861A patent/NO169014C/no unknown
- 1986-07-15 ZA ZA865262A patent/ZA865262B/xx unknown
- 1986-07-15 KR KR1019860005716A patent/KR940003495B1/ko not_active Expired - Fee Related
- 1986-07-15 CA CA000513756A patent/CA1247627A/en not_active Expired
- 1986-07-15 BE BE0/216923A patent/BE905109A/fr not_active IP Right Cessation
- 1986-07-15 DK DK335886A patent/DK335886A/da not_active Application Discontinuation
- 1986-07-15 FR FR868610295A patent/FR2585019B1/fr not_active Expired
- 1986-07-15 SU SU864027842A patent/SU1535378A3/ru active
- 1986-07-15 PH PH34013A patent/PH23459A/en unknown
- 1986-07-15 IT IT8621124A patent/IT1213103B/it active
- 1986-07-15 DE DE3623853A patent/DE3623853C2/de not_active Expired - Fee Related
- 1986-07-15 JP JP61164878A patent/JPH0780842B2/ja not_active Expired - Lifetime
- 1986-07-15 CH CH2821/86A patent/CH671958A5/de not_active IP Right Cessation
- 1986-07-16 FI FI862960A patent/FI82929C/fi not_active IP Right Cessation
- 1986-07-16 CN CN86104774A patent/CN1026984C/zh not_active Expired - Fee Related
- 1986-07-16 GB GB8617293A patent/GB2178037B/en not_active Expired
- 1986-07-16 CZ CS865411A patent/CZ277823B6/cs unknown
-
1987
- 1987-11-11 SU SU874203631A patent/SU1538893A3/ru active
Non-Patent Citations (1)
| Title |
|---|
| Nature, 1964, 203, 1064. * |
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