FI72316C - Förfarande för framställning av farmaceutiskt aktiva N2-arylsulfonyl-L -argininamider och farmaceutiskt acceptabla salter därav. - Google Patents

Förfarande för framställning av farmaceutiskt aktiva N2-arylsulfonyl-L -argininamider och farmaceutiskt acceptabla salter därav. Download PDF

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Publication number
FI72316C
FI72316C FI780073A FI780073A FI72316C FI 72316 C FI72316 C FI 72316C FI 780073 A FI780073 A FI 780073A FI 780073 A FI780073 A FI 780073A FI 72316 C FI72316 C FI 72316C
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FI
Finland
Prior art keywords
arylsulfonyl
substituted
group
acid
formula
Prior art date
Application number
FI780073A
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English (en)
Finnish (fi)
Other versions
FI780073A (fi
FI72316B (fi
Inventor
Shosuke Okamoto
Yoshikuni Tamao
Ryoji Kikumoto
Kazuo Ohkubo
Tohru Tezuka
Shinji Tonomura
Akiko Hijikata
Original Assignee
Mitsubishi Chem Ind
Shosuke Okamoto
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.)
Filing date
Publication date
Priority claimed from US05/760,745 external-priority patent/US4066773A/en
Priority claimed from US05/760,672 external-priority patent/US4093712A/en
Priority claimed from US05/760,668 external-priority patent/US4073913A/en
Priority claimed from US05/760,676 external-priority patent/US4097472A/en
Priority claimed from US05/760,929 external-priority patent/US4101653A/en
Priority claimed from US05/776,195 external-priority patent/US4097591A/en
Priority claimed from JP6650877A external-priority patent/JPS6010028B2/ja
Priority claimed from US05/804,331 external-priority patent/US4140681A/en
Priority claimed from US05/804,368 external-priority patent/US4131673A/en
Application filed by Mitsubishi Chem Ind, Shosuke Okamoto filed Critical Mitsubishi Chem Ind
Publication of FI780073A publication Critical patent/FI780073A/fi
Priority to FI842539A priority Critical patent/FI74455C/sv
Publication of FI72316B publication Critical patent/FI72316B/fi
Publication of FI72316C publication Critical patent/FI72316C/sv
Application granted granted Critical

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/16—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with acylated ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen 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
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen 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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen 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
    • C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen 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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/14—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 6 and unsubstituted in position 7
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/06—Six-membered rings
    • C07D327/08—[b,e]-condensed with two six-membered carbocyclic rings
    • 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
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06086—Dipeptides with the first amino acid being basic
    • C07K5/06095—Arg-amino acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Claims (4)

1. Förfarande för framställning av en farmaceutiskt aktiv 2 35 7231 6 N -arylsulfonyl-L-argininamid eller ett farmaceutiskt accep-tabelt sait därav, vilken förening har formeln (I): HN. %> C - N - CH.CH^CH.CHCOR (I) /· I 2 2 2[ H-N H HNS0o 2 | 2 Ar väri R är (1) COOR- (Rc ) — 5 m väri r6 är väte eller C.j-C^alkyl, varje R5 är väte eller C-j-C^-alkyl och m är ett heltal 0-2, varvid R,. kan vara i 4- eller 6-ställning; eller (2) COOH vo "N_ \ eller (3) COOH N>-\ -N O eller (4) COOH -00 7231 6 och Ar är en fenylgrupp substituerad med minst en substituent, som utgöres av amino, C^-Cg-alkylamino, C^-C^-hydroxialkyl, C^-C^0-fenylalkyl eller C^-C^-hydraxialkoxi; eller Ar är en fenylgrupp substituerad men minst en substituent, som utgöres av hydroxi, C^-Cg-alkyl eller C^-Cg-alkoxi, och med minst en substituent, som utgöres av C^-C^-alkylkarbonyl eller fenyl; eller Ar är en dibensotienyl-, 9,9-dioxodibensotienyl-, fenoxati-inyl-, kinolyl-, ftalazinyl-, fenazinyl- eller akridinyl-grupp, av vilka envar är osubstituerad eller substituerad med en eller flera hydroxi-, C^-C^-alkoxi- eller -C^-alkylgrupp-er; eller Ar är en Cg-C^g-cykloalkylfenyl-, fluorenyl-, tioxantenyl- eller 2H-kromenylgrupp, av vilka envar är osubstituerad eller substituerad med en eller flera C.-C,-alkyl-, C.-C -alkoxi- ib lb eller oxogrupper; eller Ar är en fenylgrupp substituerad med minst en substituent, som utgöres av en C^-C^-haloalkoxi- eller C2~C^-alkoxialkoxi-grupp, och möjligen är den substituerade fenylgruppen ytter-ligare substituerad med minst en substituent, som utgöres av metyl, etyl, metoxi, etoxi, hydroxi eller halogen, känne-t e c k n a t av att a) N -substituenten avlägsnas frltn en N -substituerad N - arylsulfonyl-L-argininamid med formeln: HN C - N - CH-CHoCH»CHC0R (XX) I 2 2 2I HN R" HNSO- I I 2 R' Ar väri R och Ar är definierade ovan, R' och R" är väte eller en skyddsgrupp för guanidinogruppen, och ätminstone den ena ti 37 7231 6 av grupperna R' och R" är en skyddsgrupp för guanidinogruppen, medelst syrahydrolysering eller hydrering och, om sä önskas, hydrolyseras den sä erhällna reaktionsprodukten, eller 2 b) en N -arylsulfonyl-L-arginylhalogenid med formeln HN C - N - CH^CH.CH.CHCOX (XXII) | Z Z Z j H~N H HNSO-
2. Förfarande enligt patentkravet 1,känneteck- Q n a t av att syrahydrolysen utföres genom att bringa den N -2 substituerade N -arylsulfonyl-L-argininamiden i kontakt med ett överskott av en syra vid en temperatur mellan -10 och 100°C.
2 I 2 Ar väri Ar är definierad ovan och X är halogen, omsättes med ett aminosyraderivat med formeln RH (IV) väri R är definierad ovan, och, om sä önskas, hydrolyseras den erhällna reaktionsprodukten, och, om sä önskas, omvandlas en erhällen förening med formeln I tili ett farmaceutiskt acceptabelt sait.
3. Förfarande enligt patentkravet 1,känneteck-n a t av att hydreringen utföres i ett inert reaktionslös-ningsmedel i närvaro av en aktiverande vätekatalysator i väteatmosfär vid en temperatur mellan 0°C och lösningsmedlets kokpunkt.
4. Förfarande enligt patentkravet 1,känneteck- 2 n a t av att N -arylsulfonyl-L-arginyl-halogeniden omsättes med ätminstone en ekvimolär mängd av aminosyraderivatet vid en temperatur mellan -10 och +80°C.
FI780073A 1977-01-19 1978-01-10 Förfarande för framställning av farmaceutiskt aktiva N2-arylsulfonyl-L -argininamider och farmaceutiskt acceptabla salter därav. FI72316C (sv)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FI842539A FI74455C (sv) 1977-01-19 1984-06-21 Förfarande för framställning av farmaceutiskt aktiva N2-arylsulfonyl-L -argininamider och farmaceutisktacceptabla salter därav.

Applications Claiming Priority (18)

Application Number Priority Date Filing Date Title
US05/760,676 US4097472A (en) 1974-11-08 1977-01-19 N2 -arylsulfonyl-l-argininamides and the pharmaceutically acceptable salts thereof
US05/760,668 US4073913A (en) 1974-11-08 1977-01-19 N2 -arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof
US05/760,929 US4101653A (en) 1974-11-08 1977-01-19 N2 -arylsulfonyl-argininamides and the pharmaceutically acceptable salts thereof
US05/760,745 US4066773A (en) 1974-11-08 1977-01-19 N2 -arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof
US76092977 1977-01-19
US76067677 1977-01-19
US76066877 1977-01-19
US05/760,672 US4093712A (en) 1974-11-08 1977-01-19 N2 -arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof
US76067277 1977-01-19
US76074577 1977-01-19
US05/776,195 US4097591A (en) 1974-11-08 1977-03-10 N2 -arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof
US77619577 1977-03-10
JP6650877A JPS6010028B2 (ja) 1977-06-06 1977-06-06 Ｎ↑２−アリ−ルスルホニル−ｌ−アルギニンアミド類及び薬剤として許容され得るその塩
JP6650877 1977-06-06
US80433177 1977-06-07
US05/804,331 US4140681A (en) 1974-11-08 1977-06-07 N2 -Arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof
US05/804,368 US4131673A (en) 1974-11-08 1977-06-07 N2 -arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof
US80436877 1977-06-07

Publications (3)

Publication Number Publication Date
FI780073A FI780073A (fi) 1978-07-20
FI72316B FI72316B (fi) 1987-01-30
FI72316C true FI72316C (sv) 1987-05-11

Family

ID=27577127

Family Applications (1)

Application Number Title Priority Date Filing Date
FI780073A FI72316C (sv) 1977-01-19 1978-01-10 Förfarande för framställning av farmaceutiskt aktiva N2-arylsulfonyl-L -argininamider och farmaceutiskt acceptabla salter därav.

Country Status (17)

Country Link
CA (1) CA1131621A (sv)
CH (2) CH633773A5 (sv)
DD (1) DD137352A5 (sv)
DE (1) DE2801478A1 (sv)
DK (1) DK150521C (sv)
FI (1) FI72316C (sv)
GB (1) GB1596971A (sv)
GR (1) GR60787B (sv)
IL (1) IL53685A (sv)
IT (1) IT1126229B (sv)
NL (1) NL187746C (sv)
NO (1) NO158681C (sv)
NZ (1) NZ186198A (sv)
PH (1) PH15913A (sv)
SE (1) SE452624B (sv)
SU (1) SU1181539A3 (sv)
UA (1) UA8370A1 (sv)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA794581B (en) * 1978-08-31 1981-04-29 Mitsubishi Chem Ind N 2-arylsulfonyl-l-argininamides and the pharmaceutically acceptable salts thereof
IE48623B1 (en) * 1978-08-31 1985-03-20 Mitsubishi Chem Ind Alpha-(n-arylsulfonyl-l-argininamides,processes for their preparation and pharmaceutical compositions containing these substances
GB9209032D0 (en) * 1992-04-25 1992-06-10 Ciba Geigy Ag New peptide derivatives
GB9426038D0 (en) 1994-12-22 1995-02-22 Iaf Biochem Int Low molecular weight bicyclic thrombin inhibitors
US6057314A (en) * 1995-12-21 2000-05-02 Biochem Pharma Inc. Low molecular weight bicyclic thrombin inhibitors
FR2761065B1 (fr) * 1997-03-20 2000-03-03 Synthelabo Derives de n-(arginyle)benzenesulfonamide, leur preparation et leur application en therapeutique
CN111961114A (zh) * 2020-08-03 2020-11-20 扬州中宝药业股份有限公司 一种阿加曲班中间体及其制备方法与应用

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3978045A (en) * 1973-08-13 1976-08-31 Mitsubishi Chemical Industries Ltd. N2 -dansyl-L-arginine derivatives, and the pharmaceutically acceptable acid addition salts thereof

Also Published As

Publication number Publication date
DK150521C (da) 1987-10-19
IL53685A (en) 1985-12-31
NO158681B (no) 1988-07-11
CH648293A5 (en) 1985-03-15
IT1126229B (it) 1986-05-14
NL187746C (nl) 1992-01-02
UA8370A1 (uk) 1996-03-29
CA1131621A (en) 1982-09-14
GB1596971A (en) 1981-09-03
IL53685A0 (en) 1978-03-10
DE2801478C2 (sv) 1991-01-31
NL7800448A (nl) 1978-07-21
FI780073A (fi) 1978-07-20
NL187746B (nl) 1991-08-01
NZ186198A (en) 1980-12-19
NO780191L (no) 1978-07-20
SE452624B (sv) 1987-12-07
SU1181539A3 (ru) 1985-09-23
GR60787B (en) 1978-08-28
DE2801478A1 (de) 1978-07-20
CH633773A5 (en) 1982-12-31
SE7800512L (sv) 1978-07-20
DK150521B (da) 1987-03-16
DD137352A5 (de) 1979-08-29
FI72316B (fi) 1987-01-30
DK26378A (da) 1978-07-20
PH15913A (en) 1983-04-22
NO158681C (no) 1988-10-19

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