FI83640B - Foerfarande foer framstaellning av terapeutiskt anvaendbara poly-4-aminopyrrol-2-karboxamidderivat. - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara poly-4-aminopyrrol-2-karboxamidderivat. Download PDFInfo
- Publication number
- FI83640B FI83640B FI862959A FI862959A FI83640B FI 83640 B FI83640 B FI 83640B FI 862959 A FI862959 A FI 862959A FI 862959 A FI862959 A FI 862959A FI 83640 B FI83640 B FI 83640B
- Authority
- FI
- Finland
- Prior art keywords
- methyl
- pyrrole
- carboxamido
- formula
- compound
- Prior art date
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 150
- 150000001875 compounds Chemical class 0.000 claims description 91
- -1 methyloxiranyl Chemical group 0.000 claims description 75
- 238000000034 method Methods 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 229940053202 antiepileptics carboxamide derivative Drugs 0.000 claims description 3
- 125000004069 aziridinyl group Chemical group 0.000 claims description 3
- 125000000466 oxiranyl group Chemical group 0.000 claims description 3
- 101000983970 Conus catus Alpha-conotoxin CIB Chemical group 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- RLOQBKJCOAXOLR-UHFFFAOYSA-N 1h-pyrrole-2-carboxamide Chemical compound NC(=O)C1=CC=CN1 RLOQBKJCOAXOLR-UHFFFAOYSA-N 0.000 description 37
- 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 description 36
- 229910052757 nitrogen Inorganic materials 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 238000005481 NMR spectroscopy Methods 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- PRAHCKGOTFKWKD-UHFFFAOYSA-N dimethyl(propyl)azanium;chloride Chemical compound Cl.CCCN(C)C PRAHCKGOTFKWKD-UHFFFAOYSA-N 0.000 description 16
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- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 description 14
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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
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 10
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
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- 206010039491 Sarcoma Diseases 0.000 description 4
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- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
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- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
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- 239000007884 disintegrant Substances 0.000 description 1
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- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 229960004393 lidocaine hydrochloride Drugs 0.000 description 1
- YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SWVGZFQJXVPIKM-UHFFFAOYSA-N n,n-bis(methylamino)propan-1-amine Chemical compound CCCN(NC)NC SWVGZFQJXVPIKM-UHFFFAOYSA-N 0.000 description 1
- BFDVACSKFIVAOB-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-n-methyl-4-[methyl-[4-[methyl-[4-[methyl-(4-nitro-1h-pyrrole-2-carbonyl)amino]-1h-pyrrole-2-carbonyl]amino]-1h-pyrrole-2-carbonyl]amino]-1h-pyrrole-2-carboxamide Chemical compound N1C(C(=O)N(C)CCCN(C)C)=CC(N(C)C(=O)C=2NC=C(C=2)N(C)C(=O)C=2NC=C(C=2)N(C)C(=O)C=2NC=C(C=2)[N+]([O-])=O)=C1 BFDVACSKFIVAOB-UHFFFAOYSA-N 0.000 description 1
- QYRAPNSTSXOQKF-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-n-methyl-4-nitro-1h-pyrrole-2-carboxamide Chemical compound CN(C)CCCN(C)C(=O)C1=CC([N+]([O-])=O)=CN1 QYRAPNSTSXOQKF-UHFFFAOYSA-N 0.000 description 1
- ZGKYGSOBRKYZEI-UHFFFAOYSA-N n-[5-[3-(dimethylamino)propyl-methylcarbamoyl]-1h-pyrrol-3-yl]-n-methyl-4-(oxirane-2-carbonylamino)-1h-pyrrole-2-carboxamide;hydrochloride Chemical compound Cl.N1C(C(=O)N(C)CCCN(C)C)=CC(N(C)C(=O)C=2NC=C(NC(=O)C3OC3)C=2)=C1 ZGKYGSOBRKYZEI-UHFFFAOYSA-N 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridine hydrochloride Substances [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
Classifications
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
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)
- 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)
Claims (4)
1 R1 jossa Rj, R2 ja n ovat edellä määriteltyjä ja kumpikin X 35 merkitsee samaa kuin kaavassa VIII, ja halogenoidaan kaavan IX mukainen yhdiste, ja haluttaessa kaavan I mukainen yhdiste muutetaan suolaksi. 34 83640 Förfarande för framställning av terapeutiskt an-vändbara poly-4-aminopyrrol-2-karboxamidderivat med form-5 eln I och deras farmaceutiskt godtagbara sait Is !·γ SVχχ. L ^ °Jn I1 ||'N'R2 R1 O väri n betecknar 0 eller ett heltal 1-4; 15. betecknar a) -NHR3, väri R3 betecknar a’) -CON(NO)R4, varvid R4 betecknar C1.4-alkyl, som eventuellt är substituerad med halogen; eller 20 b' ) -CO(CH2)B-R5, varvid R5 betecknar halogen, oxiranyl, metyloxiranyl eller aziridinyl; och m är 0, 1 eller 2; eller b) -NR6R7, väri R6 och R7 vardera betecknar 2-halo-25 gensubstituerad alkyl; vartdera Rx betecknar självständigt väte eller C1.4-alkyl; R2 betecknar C^-alkyl med en terminal basisk eller sur grupp, som kan utgöras av en di-C1.6-alkylamino-, amidino-eller imidazolgrupp; under förutsättning att n ej är 1 när 30 R2 betecknar -CH2CH2C(NH2 )NH; kännetecknat därav, att a) en förening med formeln V H2N^_ Γ h
35 I 1 _, H (V) Τη Y-Vtr. ί l, · J. <_ p 35 83640 väri n, Rj och R2 är definierade ovan, bringas att reagera med en förening med formeln VI O II
5 Z’-C-N(NO)R4 (VI) väri R4 är definierad ovan och Z’ är en lämnande grupp; eller b) en förening med formeln V, väri Rlf R2 och n är 10 definierade ovan, bringas att reagera med en förening med formeln VII Z-CO(CH2)bR5 (VII) 15 väri R5 och m är definierade ovan, och Z är en lämnande grupp; eller c) en förening med formeln V, väri Rlf R2 och m är definierade ovan, bringas att reagera med en förening med formeln (VIII) 20 X-CH-CH, (VIII) \ / O väri X betecknar väte eller C1.2-alkyl, varvid en förening 25 med formeln IX erhälles r η (IX) R, L I O -1 n i ά 1 *i \ väri Rj, R2 och n är definierade ovan och vardera X betecknar samma som i formeln VIII, och föreningen med formeln 35 IX halogeneras, och om sä önskas, omvandlas föreningen med formeln I tili ett sait.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8517922 | 1985-07-16 | ||
| GB858517922A GB8517922D0 (en) | 1985-07-16 | 1985-07-16 | Carboxamido derivatives |
| GB8613594 | 1986-06-04 | ||
| GB868613594A GB8613594D0 (en) | 1986-06-04 | 1986-06-04 | Poly-4-aminopyrrole-2-carboxamido derivatives |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI862959A0 FI862959A0 (fi) | 1986-07-16 |
| FI862959A7 FI862959A7 (fi) | 1987-01-17 |
| FI83640B true FI83640B (fi) | 1991-04-30 |
| FI83640C FI83640C (sv) | 1991-08-12 |
Family
ID=26289538
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI862959A FI83640C (sv) | 1985-07-16 | 1986-07-16 | Förfarande för framställning av terapeutiskt användbara poly-4-aminopy rrol-2-karboxamidderivat |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPH0780843B2 (sv) |
| KR (1) | KR930010496B1 (sv) |
| CN (1) | CN1018825B (sv) |
| AT (1) | AT387013B (sv) |
| AU (1) | AU587841B2 (sv) |
| BE (1) | BE905110A (sv) |
| CA (1) | CA1285934C (sv) |
| CH (1) | CH674206A5 (sv) |
| CS (1) | CS276981B6 (sv) |
| DE (1) | DE3623880A1 (sv) |
| DK (1) | DK335986A (sv) |
| ES (1) | ES2000502A6 (sv) |
| FI (1) | FI83640C (sv) |
| FR (1) | FR2585018B1 (sv) |
| GB (1) | GB2178036B (sv) |
| GR (1) | GR861841B (sv) |
| HU (1) | HU205949B (sv) |
| IE (1) | IE59073B1 (sv) |
| IL (1) | IL79402A (sv) |
| IT (1) | IT1196488B (sv) |
| NL (1) | NL8601837A (sv) |
| NO (1) | NO168826C (sv) |
| NZ (1) | NZ216829A (sv) |
| PH (1) | PH24714A (sv) |
| PT (1) | PT82984B (sv) |
| SE (1) | SE468642B (sv) |
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 |
| JP2000503999A (ja) * | 1996-02-02 | 2000-04-04 | フアルマシア・エ・アツプジヨン・エツセ・ピー・アー | ジスタマイシン誘導体、その調製方法、および抗腫瘍および抗ウイルス剤としてのその使用 |
| 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 (sv) | 1963-04-04 | 1966-03-23 | ||
| DE1795539A1 (de) * | 1963-07-26 | 1972-01-13 | Farmaceutici Italia | Verfahren zur Herstellung von neuen Pyrrolderivaten und ihren Salzen |
| US3420844A (en) * | 1963-07-26 | 1969-01-07 | Farmaceutici Italia | Pyrrole-2-carboxamido-propionamidines |
| BE666612A (sv) * | 1963-07-26 | 1965-11-03 | ||
| NL130086C (sv) | 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 AU AU60202/86A patent/AU587841B2/en not_active Ceased
- 1986-07-14 IE IE187586A patent/IE59073B1/en 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
- 1986-07-14 NL NL8601837A patent/NL8601837A/xx not_active Application Discontinuation
- 1986-07-14 IL IL79402A patent/IL79402A/xx not_active IP Right Cessation
- 1986-07-14 HU HU862904A patent/HU205949B/hu not_active IP Right Cessation
- 1986-07-15 CH CH2820/86A patent/CH674206A5/de not_active IP Right Cessation
- 1986-07-15 IT IT21125/86A patent/IT1196488B/it active
- 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 FR FR868610294A patent/FR2585018B1/fr not_active Expired
- 1986-07-15 JP JP61164879A patent/JPH0780843B2/ja not_active Expired - Lifetime
- 1986-07-15 DK DK335986A patent/DK335986A/da not_active Application Discontinuation
- 1986-07-15 KR KR1019860005715A patent/KR930010496B1/ko not_active Expired - Fee Related
- 1986-07-15 NO NO862860A patent/NO168826C/no unknown
- 1986-07-15 CA CA000513760A patent/CA1285934C/en not_active Expired - Lifetime
- 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 PH PH34014A patent/PH24714A/en unknown
- 1986-07-16 GB GB8617292A patent/GB2178036B/en not_active Expired
- 1986-07-16 CN CN86104787A patent/CN1018825B/zh not_active Expired
- 1986-07-16 FI FI862959A patent/FI83640C/sv not_active IP Right Cessation
- 1986-07-16 CS CS865412A patent/CS276981B6/cs unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC | Transfer of assignment of patent |
Owner name: PHARMACIA & UPJOHN S.P.A. |
|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: PHARMACIA & UPJOHN S., P.A. |