DE2644820A1 - Cancerostatisch und immunstimulierend wirkende 1-(n-acyl-carbamoyl)-2-cyanaziridine sowie verfahren zur herstellung derselben - Google Patents
Cancerostatisch und immunstimulierend wirkende 1-(n-acyl-carbamoyl)-2-cyanaziridine sowie verfahren zur herstellung derselbenInfo
- Publication number
- DE2644820A1 DE2644820A1 DE19762644820 DE2644820A DE2644820A1 DE 2644820 A1 DE2644820 A1 DE 2644820A1 DE 19762644820 DE19762644820 DE 19762644820 DE 2644820 A DE2644820 A DE 2644820A DE 2644820 A1 DE2644820 A1 DE 2644820A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- carbamoyl
- formula
- halogen
- alkoxy
- 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.)
- Withdrawn
Links
- 230000003327 cancerostatic effect Effects 0.000 title description 5
- 230000003308 immunostimulating effect Effects 0.000 title description 3
- -1 sulphamoyl Chemical group 0.000 claims abstract description 20
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 150000002367 halogens Chemical class 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 12
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 8
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000012948 isocyanate Substances 0.000 claims description 10
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- 239000002253 acid Substances 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
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- 238000000034 method Methods 0.000 claims description 4
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- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 230000003213 activating effect Effects 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 150000001540 azides Chemical class 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
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- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
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- OCKPROYBCPQWJO-UHFFFAOYSA-N acetyl isocyanate Chemical compound CC(=O)N=C=O OCKPROYBCPQWJO-UHFFFAOYSA-N 0.000 abstract description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 2
- RMSRKYVNQYEPHO-UHFFFAOYSA-N 2-cyanoaziridine-1-carboxamide Chemical compound NC(=O)N1CC1C#N RMSRKYVNQYEPHO-UHFFFAOYSA-N 0.000 abstract 1
- 231100001231 less toxic Toxicity 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
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- 239000002244 precipitate Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- MOVMEFHWBOWMFU-UHFFFAOYSA-N 2-chloroacetyl isocyanate Chemical compound ClCC(=O)N=C=O MOVMEFHWBOWMFU-UHFFFAOYSA-N 0.000 description 3
- GMYKYCKUEYTTFJ-UHFFFAOYSA-N 3-methylaziridine-2-carbonitrile Chemical compound CC1NC1C#N GMYKYCKUEYTTFJ-UHFFFAOYSA-N 0.000 description 3
- PBNPTRKEHUFRPP-UHFFFAOYSA-N 3-phenylaziridine-2-carbonitrile Chemical compound N#CC1NC1C1=CC=CC=C1 PBNPTRKEHUFRPP-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
- 238000009835 boiling Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
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- 159000000000 sodium salts Chemical class 0.000 description 3
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- MJYZITPAOSTIQH-UHFFFAOYSA-N 2-cyano-n-(2,2,2-trichloroacetyl)aziridine-1-carboxamide Chemical compound ClC(Cl)(Cl)C(=O)NC(=O)N1CC1C#N MJYZITPAOSTIQH-UHFFFAOYSA-N 0.000 description 2
- OQWRGZAEYVLUAX-UHFFFAOYSA-N 2-cyano-n-(2,2-dichloroacetyl)aziridine-1-carboxamide Chemical compound ClC(Cl)C(=O)NC(=O)N1CC1C#N OQWRGZAEYVLUAX-UHFFFAOYSA-N 0.000 description 2
- FZRXBDHZYZWNBS-UHFFFAOYSA-N 2-cyano-n-(3-nitrobenzoyl)aziridine-1-carboxamide Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)NC(=O)N2C(C2)C#N)=C1 FZRXBDHZYZWNBS-UHFFFAOYSA-N 0.000 description 2
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- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 2
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- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical compound O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 description 1
- SFWQPYSIXMKRKF-UHFFFAOYSA-N n-(oxomethylidene)ethanesulfonamide Chemical compound CCS(=O)(=O)N=C=O SFWQPYSIXMKRKF-UHFFFAOYSA-N 0.000 description 1
- OUPLTJDZPQZRBW-UHFFFAOYSA-N n-(oxomethylidene)methanesulfonamide Chemical compound CS(=O)(=O)N=C=O OUPLTJDZPQZRBW-UHFFFAOYSA-N 0.000 description 1
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- HERPTUDGZSUAHF-UHFFFAOYSA-N n-butylsulfonyl-2-cyanoaziridine-1-carboxamide Chemical compound CCCCS(=O)(=O)NC(=O)N1CC1C#N HERPTUDGZSUAHF-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
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- 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
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- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
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- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
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- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
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- 235000011152 sodium sulphate Nutrition 0.000 description 1
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- 230000000638 stimulation Effects 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/16—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms
- C07D203/20—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms by carbonic acid, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/22—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
- C07D203/24—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three 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
- C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
- C07D317/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/564—Three-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (26)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19762644820 DE2644820A1 (de) | 1976-10-05 | 1976-10-05 | Cancerostatisch und immunstimulierend wirkende 1-(n-acyl-carbamoyl)-2-cyanaziridine sowie verfahren zur herstellung derselben |
CA287,572A CA1092606A (fr) | 1976-10-05 | 1977-09-27 | 1-(n-acylcarbamoyl)-2-cyano-aziridines et procede de preparation |
CS776290A CS199711B2 (en) | 1976-10-05 | 1977-09-28 | Method of producing 1-/n-acylcarbamoyl/-2-cyanaziridines |
US05/838,426 US4282212A (en) | 1976-10-05 | 1977-09-30 | Immune-stimulating 1-(N-acylcarbamoyl)-2-cyanoaziridines |
PT67108A PT67108B (de) | 1976-10-05 | 1977-10-03 | Cancerostatisch und immunstimulierend wirkende 1-(n-acyl-carbamoil)-2-cyanaziridine sowie verfahren zur herstellung derselben |
GB40926/77A GB1547513A (en) | 1976-10-05 | 1977-10-03 | 1-(n-acylcarbamoyl)-2-cyanoaziridines |
LU7778237A LU78237A1 (fr) | 1976-10-05 | 1977-10-03 | |
NL7710790A NL7710790A (nl) | 1976-10-05 | 1977-10-03 | Werkwijze ter bereiding van cancerostatisch en immunostimulerend werkende 1-(n-acylcarbamoyl)- -2-cyanaziridinen. |
NZ185319A NZ185319A (en) | 1976-10-05 | 1977-10-03 | 1-(n-acylcarbamoyl)-2-cyanoaziridines and pharmaceutical compositions |
DD7700201316A DD131927A5 (de) | 1976-10-05 | 1977-10-03 | Verfahren zur herstellung cancerostatisch und immunstimulierend wirkender 1-(n-acyl-carbamoyl)-2-cyanaziridine |
IT28225/77A IT1087759B (it) | 1976-10-05 | 1977-10-03 | 1-(n-acil-carbamoil)-2-cianaziridin e con attivita' cancerostatica e immunostimolante e processi per la loro preparazione |
ES462890A ES462890A1 (es) | 1976-10-05 | 1977-10-04 | Procedimiento para la preparacion de 1-(n-acil-carbamoil)-2-cianazi-ridinas con efecto cancerostatico y estimulador de inmunidad. |
AT706577A AT356129B (de) | 1976-10-05 | 1977-10-04 | Verfahren zur herstellung von substituierten 1-carbamoyl-2-cyanaziridinen |
NO773377A NO773377L (no) | 1976-10-05 | 1977-10-04 | Fremgangsmaate ved fremstilling av 1-(n-acyl-carbamoyl)-2-cyanaziridiner |
DK438177A DK438177A (da) | 1976-10-05 | 1977-10-04 | Cancerostatisk og immunstimulerende 1-(n-acylcarbamoyl)-2-cyanaziridiner samt fremgangsmaade til deres fremstilling |
BE181441A BE859355A (fr) | 1976-10-05 | 1977-10-04 | 1-(n-acyl-carbamoyl)-2-cyanaziridines a action oncostatique et immuno-stimulatrice et procedes pour leur preparation |
FI772924A FI772924A (fi) | 1976-10-05 | 1977-10-04 | Foerfarande foer framstaellning av 1-(n-acylkarbomoyl)-2-cyanaziridiner med cancerostatisk och immunstimulerande verkan |
IE2023/77A IE45782B1 (en) | 1976-10-05 | 1977-10-04 | 1-(n-acylcarbamoyl)-2-cyanoziridines |
PL1977201285A PL110162B1 (en) | 1976-10-05 | 1977-10-04 | Method of producing new 1-/n-acylocarbamylo/-2-cyanoazyridins |
AU29314/77A AU2931477A (en) | 1976-10-05 | 1977-10-04 | 1(n-acylcarbamoyl)-2-cyanoaziridines |
SE7711093A SE7711093L (sv) | 1976-10-05 | 1977-10-04 | 1-(n-acyl-karbamoyl)-2-cyanaziridiner |
ZA00775904A ZA775904B (en) | 1976-10-05 | 1977-10-04 | New 1-(n-acylcarbamoyl)-2-cyanoaziridines and the preparation thereof |
FR7729924A FR2367062A1 (fr) | 1976-10-05 | 1977-10-05 | Derives 1-(n-acylcarbamoyl) 2-cyano-aziridines ayant une action cancerostatique et immunostimulatrice et procede pour leur preparation |
AR269465A AR217085A1 (es) | 1976-10-05 | 1977-10-05 | Procedimiento para preparar 1-(n-acil-carbamoil)-2-cianaziridinas |
JP11989577A JPS5350153A (en) | 1976-10-05 | 1977-10-05 | Production of 11*nnacyll carbamoyl**22cyanaziridine and pharmaceutical agent containing same with antii cancer and immune stimulating action |
OA56292A OA05778A (fr) | 1976-10-05 | 1977-10-05 | Procédé de préparation de dérivés l-(N-acylcarbamoyl) 2-cyano-aziridines. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19762644820 DE2644820A1 (de) | 1976-10-05 | 1976-10-05 | Cancerostatisch und immunstimulierend wirkende 1-(n-acyl-carbamoyl)-2-cyanaziridine sowie verfahren zur herstellung derselben |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2644820A1 true DE2644820A1 (de) | 1978-04-06 |
Family
ID=5989674
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19762644820 Withdrawn DE2644820A1 (de) | 1976-10-05 | 1976-10-05 | Cancerostatisch und immunstimulierend wirkende 1-(n-acyl-carbamoyl)-2-cyanaziridine sowie verfahren zur herstellung derselben |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE859355A (fr) |
DE (1) | DE2644820A1 (fr) |
LU (1) | LU78237A1 (fr) |
ZA (1) | ZA775904B (fr) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2399840A1 (fr) * | 1977-08-12 | 1979-03-09 | Boehringer Mannheim Gmbh | Application de la 2-cyano-aziridine et de ses derives a l'immunostimulation |
EP0014976A1 (fr) * | 1979-02-21 | 1980-09-03 | Roche Diagnostics GmbH | 2-Cyanaziridines N-substituées, procédés pour leur préparation et médicaments les contenant ainsi que les aziridines-2-carbonamides substituées correspondantes et leur préparation |
US4376731A (en) * | 1978-01-31 | 1983-03-15 | Boehringer Mannheim Gmbh | 1-Aziridine carboxylic acid derivatives with immunostimulant activity |
US4935413A (en) * | 1984-07-03 | 1990-06-19 | Nippon Paint Co., Ltd. | Carbamate physical property-improving reagent |
-
1976
- 1976-10-05 DE DE19762644820 patent/DE2644820A1/de not_active Withdrawn
-
1977
- 1977-10-03 LU LU7778237A patent/LU78237A1/xx unknown
- 1977-10-04 ZA ZA00775904A patent/ZA775904B/xx unknown
- 1977-10-04 BE BE181441A patent/BE859355A/fr unknown
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2399840A1 (fr) * | 1977-08-12 | 1979-03-09 | Boehringer Mannheim Gmbh | Application de la 2-cyano-aziridine et de ses derives a l'immunostimulation |
US4376731A (en) * | 1978-01-31 | 1983-03-15 | Boehringer Mannheim Gmbh | 1-Aziridine carboxylic acid derivatives with immunostimulant activity |
EP0014976A1 (fr) * | 1979-02-21 | 1980-09-03 | Roche Diagnostics GmbH | 2-Cyanaziridines N-substituées, procédés pour leur préparation et médicaments les contenant ainsi que les aziridines-2-carbonamides substituées correspondantes et leur préparation |
US4935413A (en) * | 1984-07-03 | 1990-06-19 | Nippon Paint Co., Ltd. | Carbamate physical property-improving reagent |
US5354495A (en) * | 1984-07-03 | 1994-10-11 | Nippon Paint Co., Ltd. | Alkenoylcarbamate compounds as elasticity, adhesion, and dispersibility enhancer |
Also Published As
Publication number | Publication date |
---|---|
ZA775904B (en) | 1978-06-28 |
BE859355A (fr) | 1978-04-04 |
LU78237A1 (fr) | 1979-02-02 |
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