CH507277A - Verfahren zur Herstellung neuer substituierter 3-Amino-sydnonimine - Google Patents

Verfahren zur Herstellung neuer substituierter 3-Amino-sydnonimine

Info

Publication number: CH507277A
Authority: CH; Switzerland
Prior art keywords: sydnonimine; alkyl; substituted; amino; acid
Prior art date: 1966-08-09

Application number

CH1092567A

Other languages

German (de)

English (en)

Inventor

Manfred Dr Goetz

Karl Dr Zeile

Kurt Dr Freier

Original Assignee

Boehringer Sohn Ingelheim

Priority date (The priority date 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 date listed.)

1966-08-09

Filing date

1967-08-03

Publication date

1971-05-15

1967-08-03 Application filed by Boehringer Sohn Ingelheim filed Critical Boehringer Sohn Ingelheim

1971-05-15 Publication of CH507277A publication Critical patent/CH507277A/de

Links

-1 CN- Chemical group 0.000 claims abstract description 27
150000001875 compounds Chemical class 0.000 claims abstract description 17
239000002253 acid Substances 0.000 claims abstract description 15
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 10
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 9
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
150000003839 salts Chemical class 0.000 claims abstract description 6
QVZILVCJQMNOLN-UHFFFAOYSA-N 5-imino-1-oxa-3-azonia-2-azanidacyclopent-3-en-3-amine Chemical class N[N+]1=CC(=N)O[N-]1 QVZILVCJQMNOLN-UHFFFAOYSA-N 0.000 claims abstract description 5
125000002252 acyl group Chemical group 0.000 claims abstract description 5
125000004423 acyloxy group Chemical group 0.000 claims abstract description 5
125000003118 aryl group Chemical group 0.000 claims abstract description 5
125000005843 halogen group Chemical group 0.000 claims abstract description 5
125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 3
125000002947 alkylene group Chemical group 0.000 claims abstract description 3
125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
125000005842 heteroatom Chemical group 0.000 claims abstract description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 3
125000003107 substituted aryl group Chemical group 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 14
229910052757 nitrogen Inorganic materials 0.000 claims description 8
239000003795 chemical substances by application Substances 0.000 claims description 6
GSKDBLIBBOYOFU-UHFFFAOYSA-N oxadiazol-5-amine Chemical class NC1=CN=NO1 GSKDBLIBBOYOFU-UHFFFAOYSA-N 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
150000008065 acid anhydrides Chemical class 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
BQIKRTGTPBOIMK-UHFFFAOYSA-N [O]C[O] Chemical compound [O]C[O] BQIKRTGTPBOIMK-UHFFFAOYSA-N 0.000 claims description 2
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
SRANPMHVZAXTBA-UHFFFAOYSA-N n-(cyanomethyl)nitrous amide Chemical class O=NNCC#N SRANPMHVZAXTBA-UHFFFAOYSA-N 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 1
150000002148 esters Chemical class 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
150000007522 mineralic acids Chemical class 0.000 abstract description 3
150000007524 organic acids Chemical class 0.000 abstract description 3
230000036772 blood pressure Effects 0.000 abstract description 2
210000003169 central nervous system Anatomy 0.000 abstract description 2
230000000694 effects Effects 0.000 abstract description 2
125000001188 haloalkyl group Chemical group 0.000 abstract description 2
235000005985 organic acids Nutrition 0.000 abstract description 2
101100134922 Gallus gallus COR5 gene Proteins 0.000 abstract 1
239000003925 fat Substances 0.000 abstract 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 74
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
239000000243 solution Substances 0.000 description 26
239000000203 mixture Substances 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
238000001816 cooling Methods 0.000 description 11
238000003756 stirring Methods 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
239000012043 crude product Substances 0.000 description 8
238000000354 decomposition reaction Methods 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 7
235000010288 sodium nitrite Nutrition 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
239000008098 formaldehyde solution Substances 0.000 description 6
150000002832 nitroso derivatives Chemical class 0.000 description 6
239000000377 silicon dioxide Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
238000010828 elution Methods 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
YBOQSVRDMSNIOX-UHFFFAOYSA-N 5-imino-n,n-dimethyl-1-oxa-3-azonia-2-azanidacyclopent-3-en-3-amine Chemical compound CN(C)[N+]1=CC(=N)O[N-]1 YBOQSVRDMSNIOX-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
150000002429 hydrazines Chemical class 0.000 description 3
UPVLRUMEBXYJMQ-UHFFFAOYSA-N 1,1-bis(prop-2-enyl)hydrazine Chemical compound C=CCN(N)CC=C UPVLRUMEBXYJMQ-UHFFFAOYSA-N 0.000 description 2
MVFWHQWYMIVZJF-UHFFFAOYSA-N 3-piperidin-1-yl-1-oxa-3-azonia-2-azanidacyclopent-3-en-5-imine;hydrochloride Chemical compound Cl.[N-]1OC(=N)C=[N+]1N1CCCCC1 MVFWHQWYMIVZJF-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
FHKRFUHAZOWBHF-UHFFFAOYSA-N CC1=CC=CC(CN[N+]([N-]O2)=CC2=N)=C1 Chemical compound CC1=CC=CC(CN[N+]([N-]O2)=CC2=N)=C1 FHKRFUHAZOWBHF-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000002026 chloroform extract Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
FTBYHABJPALDSP-UHFFFAOYSA-N 1-benzyl-1-methylhydrazine Chemical compound CN(N)CC1=CC=CC=C1 FTBYHABJPALDSP-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
FRNYRFYJIDIVGM-UHFFFAOYSA-N 3-(2-benzylpiperidin-1-yl)-1-oxa-3-azonia-2-azanidacyclopent-3-en-5-imine Chemical compound [N-]1OC(=N)C=[N+]1N1C(CC=2C=CC=CC=2)CCCC1 FRNYRFYJIDIVGM-UHFFFAOYSA-N 0.000 description 1
AAAMRTNHVAUXMM-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)-1-oxa-3-azonia-2-azanidacyclopent-3-en-5-imine Chemical compound C1CN(C)CCN1[N+]1=CC(=N)O[N-]1 AAAMRTNHVAUXMM-UHFFFAOYSA-N 0.000 description 1
JJMQIJNYXQVIKP-UHFFFAOYSA-N 3-(azepan-1-yl)-1-oxa-3-azonia-2-azanidacyclopent-3-en-5-imine Chemical compound [N-]1OC(=N)C=[N+]1N1CCCCCC1 JJMQIJNYXQVIKP-UHFFFAOYSA-N 0.000 description 1
NCIGWPHMDJUFHR-UHFFFAOYSA-N 3-ethyl-1-oxa-3-azonia-2-azanidacyclopent-3-en-5-imine Chemical compound CC[N+]1=CC(=N)O[N-]1 NCIGWPHMDJUFHR-UHFFFAOYSA-N 0.000 description 1
WNCAUPVVPFCLCG-UHFFFAOYSA-N 3-piperidin-1-yl-1-oxa-3-azonia-2-azanidacyclopent-3-en-5-imine Chemical compound [N-]1OC(=N)C=[N+]1N1CCCCC1 WNCAUPVVPFCLCG-UHFFFAOYSA-N 0.000 description 1
OVPSWZPKCZYNJW-UHFFFAOYSA-N 3-pyrrolidin-1-yl-1-oxa-3-azonia-2-azanidacyclopent-3-en-5-imine Chemical compound [N-]1OC(=N)C=[N+]1N1CCCC1 OVPSWZPKCZYNJW-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
CHDAZZVWBQGPDK-UHFFFAOYSA-N 4-methyl-3-piperidin-1-yl-1-oxa-3-azonia-2-azanidacyclopent-3-en-5-imine Chemical compound [N-]1OC(=N)C(C)=[N+]1N1CCCCC1 CHDAZZVWBQGPDK-UHFFFAOYSA-N 0.000 description 1
RVBPWHROVRSEMW-UHFFFAOYSA-N 5-imino-n-(3-methylcyclohexyl)-1-oxa-3-azonia-2-azanidacyclopent-3-en-3-amine Chemical compound C1C(C)CCCC1N[N+]1=CC(=N)O[N-]1 RVBPWHROVRSEMW-UHFFFAOYSA-N 0.000 description 1
OLEFNFXYGGTROA-UHFFFAOYSA-N 5-nitrofuran-2-carbonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)O1 OLEFNFXYGGTROA-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
YDRXPASRJIFKDB-UHFFFAOYSA-N C[N+]=1[N-]OC(C=1N1CCNCC1)=N Chemical compound C[N+]=1[N-]OC(C=1N1CCNCC1)=N YDRXPASRJIFKDB-UHFFFAOYSA-N 0.000 description 1
AZWXZWPKCZBUNO-UHFFFAOYSA-N C[N+]=1[N-]OC(C=1NCC#C)=N Chemical compound C[N+]=1[N-]OC(C=1NCC#C)=N AZWXZWPKCZBUNO-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
210000000577 adipose tissue Anatomy 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
UGBKOURNNQREPE-UHFFFAOYSA-N azepan-1-amine Chemical compound NN1CCCCCC1 UGBKOURNNQREPE-UHFFFAOYSA-N 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229960004106 citric acid Drugs 0.000 description 1
XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical class OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical compound N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
FKDHHVKWGRFRTG-UHFFFAOYSA-N linsidomine Chemical compound [N-]1OC(=N)C=[N+]1N1CCOCC1 FKDHHVKWGRFRTG-UHFFFAOYSA-N 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229940098895 maleic acid Drugs 0.000 description 1
239000000155 melt Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
NMAHYUUGFRBVHB-UHFFFAOYSA-N n,n-dibenzyl-5-imino-1-oxa-3-azonia-2-azanidacyclopent-3-en-3-amine Chemical compound [N-]1OC(=N)C=[N+]1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 NMAHYUUGFRBVHB-UHFFFAOYSA-N 0.000 description 1
PROIAHBAGLBNFM-UHFFFAOYSA-N n,n-diethyl-5-imino-1-oxa-3-azonia-2-azanidacyclopent-3-en-3-amine Chemical compound CCN(CC)[N+]1=CC(=N)O[N-]1 PROIAHBAGLBNFM-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
239000008023 pharmaceutical filler Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000047 product Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
230000000894 saliuretic effect Effects 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1

Classifications

- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/04—1,2,3-Oxadiazoles; Hydrogenated 1,2,3-oxadiazoles
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)

CH1092567A 1966-08-09 1967-08-03 Verfahren zur Herstellung neuer substituierter 3-Amino-sydnonimine CH507277A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEB0088408		1966-08-09

Publications (1)

Publication Number	Publication Date
CH507277A true CH507277A (de)	1971-05-15

Family

ID=6984280

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1092567A CH507277A (de)	1966-08-09	1967-08-03	Verfahren zur Herstellung neuer substituierter 3-Amino-sydnonimine

Country Status (16)

Country	Link
JP (1)	JPS537433B1 (fr)
BE (1)	BE702448A (fr)
BG (1)	BG15571A3 (fr)
CA (1)	CA925083A (fr)
CH (1)	CH507277A (fr)
DE (1)	DE1670127A1 (fr)
DK (1)	DK126594B (fr)
ES (1)	ES343818A1 (fr)
FI (1)	FI49420C (fr)
FR (2)	FR1551013A (fr)
GB (1)	GB1198283A (fr)
IL (1)	IL28432A (fr)
NL (1)	NL153195B (fr)
PH (1)	PH10178A (fr)
SE (1)	SE343304B (fr)
YU (1)	YU34691B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2930736A1 (de) *	1979-07-28	1981-02-12	Cassella Ag	Pharmakologisch wirksame, substituierte 3-amino-sydnonimine, verfahren zu ihrer herstellung und ihre verwendung
DE3837327A1 (de) *	1988-11-03	1990-05-10	Cassella Ag	Substituierte 3-aminosydnonimine, verfahren zu ihrer herstellung und ihre verwendung
DE3921460A1 (de) *	1989-06-30	1991-01-03	Cassella Ag	Substituierte 3-aminosydnonimine, verfahren zu ihrer herstellung und ihre verwendung
DE3921796A1 (de) *	1989-07-03	1991-01-17	Cassella Ag	Substituierte 3-aminosydnonimine, verfahren zu ihrer herstellung und ihre verwendung
DE4025604A1 (de) *	1990-08-13	1992-02-20	Cassella Ag	3-dicyclohexylamino-sydnonimine, verfahren zu ihrer herstellung und ihre verwendung
DE4028679A1 (de) *	1990-09-10	1992-03-19	Cassella Ag	Substituierte 3-aminosydnonimine, verfahren zu ihrer herstellung und ihre verwendung
WO1993018767A1 (fr) *	1992-03-24	1993-09-30	Cassella Aktiengesellschaft	Utilisation de sydnonimines pour traiter les troubles de l'erection
DE4337335A1 (de) *	1993-11-02	1995-05-04	Cassella Ag	Verfahren zur Herstellung von Sydnoniminium-hydrogensulfaten

1966
- 1966-08-09 DE DE19661670127 patent/DE1670127A1/de not_active Ceased
1967
- 1967-07-28 SE SE10943/67A patent/SE343304B/xx unknown
- 1967-07-31 GB GB35049/67A patent/GB1198283A/en not_active Expired
- 1967-08-01 IL IL6728432A patent/IL28432A/en unknown
- 1967-08-03 CH CH1092567A patent/CH507277A/de not_active IP Right Cessation
- 1967-08-03 CA CA996993A patent/CA925083A/en not_active Expired
- 1967-08-04 ES ES343818A patent/ES343818A1/es not_active Expired
- 1967-08-05 BG BG008440A patent/BG15571A3/bg unknown
- 1967-08-07 FI FI672132A patent/FI49420C/fi active
- 1967-08-08 YU YU1565/67A patent/YU34691B/xx unknown
- 1967-08-08 BE BE702448D patent/BE702448A/xx not_active IP Right Cessation
- 1967-08-08 DK DK404167AA patent/DK126594B/da not_active IP Right Cessation
- 1967-08-09 NL NL676710945A patent/NL153195B/xx not_active IP Right Cessation
- 1967-08-09 JP JP5076167A patent/JPS537433B1/ja active Pending
- 1967-08-09 FR FR1551013D patent/FR1551013A/fr not_active Expired
- 1967-11-09 FR FR127616A patent/FR8428M/fr not_active Expired
1972
- 1972-08-21 PH PH13823A patent/PH10178A/en unknown

Also Published As

Publication number	Publication date
GB1198283A (en)	1970-07-08
FI49420C (fi)	1975-06-10
BG15571A3 (bg)	1976-06-21
BE702448A (fr)	1968-02-08
ES343818A1 (es)	1968-12-01
FI49420B (fr)	1975-02-28
FR1551013A (fr)	1968-12-27
YU34691B (en)	1979-12-31
JPS537433B1 (fr)	1978-03-17
SE343304B (sv)	1972-03-06
PH10178A (en)	1976-09-16
DE1670127A1 (de)	1970-12-03
DK126594B (da)	1973-07-30
NL6710945A (fr)	1968-02-12
FR8428M (fr)	1971-07-08
CA925083A (en)	1973-04-24
NL153195B (nl)	1977-05-16
IL28432A (en)	1972-01-27
YU156567A (en)	1979-07-10

Legal Events

Date	Code	Title	Description
1984-04-30	PL	Patent ceased
1984-12-14	AEN	Scope or validity of the patent modified	Free format text: DIE PATENTE SIND AM 841112 GESTUETZT AUF DIE EINGEREICHTEN WIEDEREINSETZUNGSGESUCHE AUF GRUND VON ART. 47 PATG WIEDER IN KRAFT GESETZT WORDEN.
1987-10-30	PL	Patent ceased

Publication	Publication Date	Title
DE2452691A1 (de)	1975-05-15	2,6-disubstituierte phenylaminoguanidinverbindungen
DE1620501A1 (de)	1970-04-16	Neue Sydnonimin-Derivate und Verfahren zu ihrer Herstellung
DE1214674B (de)	1966-04-21	Verfahren zur Herstellung von Guanidinderivaten
DE1044806B (de)	1958-11-27	Verfahren zur Herstellung von wasserloeslichen Derivaten der Tetracycline
CH507277A (de)	1971-05-15	Verfahren zur Herstellung neuer substituierter 3-Amino-sydnonimine
DE1239692B (de)	1967-05-03	Verfahren zur Herstellung von 3-(alpha-Arylalkyl)-sydnoniminen, ihren Salzen und N-Acylderivaten
DE1111208B (de)	1961-07-20	Verfahren zur Herstellung von hustenreizstillend wirkenden, basisch substituierten Diphenylcarbinolestern
AT275514B (de)	1969-10-27	Verfahren zur Herstellung neuer substituierter 3-Amino-sydnonimine und deren Salze
CH610330A5 (en)	1979-04-12	Process for the preparation of novel ergopeptins
DE2359537C2 (de)	1984-06-14	6-Chlor-5-cyclohexylindan-1-carbohydroxamsäure, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
EP0075141A1 (fr)	1983-03-30	Dérivés de l'acide 1,2,5-oxadiazol-3,4-dicarboxylique, procédé pour leur fabrication, leur application et préparations pharmaceutiques les contenant
DE2330218C2 (de)	1982-11-18	Verfahren zur Herstellung von 2H-3- Isochinolonen
DE2747122A1 (de)	1978-04-27	Derivate von 6-(m-aminophenyl)-2, 3,5,6-tetrahydroimidazo eckige klammer auf 2,1-b eckige klammer zu -thiazol, verfahren zu ihrer herstellung und ihre verwendung
EP0438795A1 (fr)	1991-07-31	Di(nitroxyalkyl)amides des acides pyridine-2,4- et 2,5-dicarboxyliques, procÀ©dés pour leur préparation et leur utilisation
AT250338B (de)	1966-11-10	Verfahren zur Herstellung neuer, basischer Derivate von substituierten Benzofuran-2-carbonsäuren und deren Salzen
DE1618310C3 (fr)	1974-11-28
DE68919950T2 (de)	1995-06-22	S-(N-Alkoxycarbonyl, N-substituierte)aminomethylisothioharnstoff-Derivat.
DE1695757C3 (de)	1977-11-24	Pyridinmethanolcarbamate und Verfahren zu deren Herstellung
AT210886B (de)	1960-08-25	Verfahren zur Herstellung von neuen, basisch substituierten Diphenylcarbinolestern und deren Salzen
CH549043A (de)	1974-05-15	Verfahren zur herstellung neuer substituierter 3-aminosydnonimine.
DE1695695C3 (de)	1974-06-20	Verfahren zur Herstellung von 2-Aminofuro eckige Klammer auf 2,3-d eckige Klammer zu thiazolen
AT226709B (de)	1963-04-10	Verfahren zur Herstellung von neuen kondensierten Dihydropyrazinonen-(2) oder von deren Salzen bzw. quaternären Ammoniumsalzen
DE1595903C (de)	1972-10-05	1-Substituierte 2,6-Dimethyl-4-phenylpiperazine
AT337682B (de)	1977-07-11	Verfahren zur herstellung von neuen benzocycloalkencarbonsauren sowie ihren estern und salzen
AT215417B (de)	1961-06-12	Verfahren zur Herstellung neuer N-Carbalkoxy- bzw. -aralkoxyalkyl-β-(3,4-dihydroxyphenyl)-β-hydroxyäthylamine und deren Salze