DK165003B - Chlorsulfat - Google Patents

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DK165003B
DK165003B DK198191A DK198191A DK165003B DK 165003 B DK165003 B DK 165003B DK 198191 A DK198191 A DK 198191A DK 198191 A DK198191 A DK 198191A DK 165003 B DK165003 B DK 165003B
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Bruce Eliot Maryanoff
Joseph Francis Gardocki
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Mcneilab Inc
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    • 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
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
    • C07H9/02—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing only oxygen as ring hetero atoms
    • C07H9/04—Cyclic acetals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • 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
    • 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
    • C07D309/06—Radicals substituted by oxygen atoms

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  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Ophthalmology & Optometry (AREA)
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  • Pain & Pain Management (AREA)
  • Neurosurgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Saccharide Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Medicinal Preparation (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Hydrogenated Pyridines (AREA)

Description

DK 165003B
i
Den foreliggende opfindelse angår hidtil ukendte chlorsulfater med formlen RCI^OSi^Cl, hvor R har formlen (III) R, R, hvori R2, R3, R4 og Rg er, uafhængigt af hinanden, hydrogen eller lavere alkyl og, når X er CH2, er R^ og R5 eventuelt alkengrupper, der tilsammen danner en benzenring og, når X er oxygen, danner R2 og R^ og/ 10 eller R4 og Rg eventuelt en methylendioxygruppe med formel (II) R6 o- <n> r7 o— 15 hvori
Rg og Rj, som er ens eller forskellige, er hydrogen, lavere al kyl eller al kyl, som tilsammen danner en cyclopentyl- eller cyclohexylring.
De omhandlede chlorsulfater er nyttige som mellemprodukter til fremstilling af lægemiddelaktive sulfamater som nærmere diskuteret i det 20 følgende.
Sulfamater med forskellige strukturer, inklusive sådanne, der afledes af monosaccharider, er beskrevet i referencer såsom N.K.
Kochetkow, et al., i Zhurnal Obshchei Kimii, bind 41, nr. 8, 1866-1871 (1971), bind 42, nr. 12, 2755-2757 (1972) og bind 44, nr. 4, 871-875 25 (1974), og i Doklady Akademii Nauk SSR, bind 216, nr. 1, 97-100 (1974); T. Tsuchiya et al., i Tetrahedron Letters, nr. 36, 3365-3368 (1978); og A.F. Hirsch i Journal of Medicinal Chemistry, 24, 901-903 (1981), samt US-patentskrift nr. 4.075.351.
Det har nu vist sig, at sulfamater med formel (I) 30 /—X. CH.OSO.NHR, R, Ri hvori X er 0 eller CH2 og Rp R2, R3, R^ og Rg er som defineret i det 35 følgende, besidder anti-konvulsivisk aktivitet i pattedyr og derfor er anvendelige til behandling af sygdomstilstande såsom epilepsi og glaukom.
Sul famaterne har den følgende formel (I) 2 DK 165003 B i } i / \-CHjOSOjNHR, ! ‘Λ-Λ. (I) !
R«, R3 I
hvori i 5 X er CH2 eller oxygen. !
Rj er hydrogen eller al kyl, og R2, R3, R4 og Rg, uafhængigt af hinanden, er hydrogen eller lavere al kyl og, når X er CH2, er R^ og Rg eventuelt alkengrupper, der tilsammen danner en benzenring og, når X er oxygen, danner R2 og R3 og/ 10 eller R4 og Rg eventuelt en methyl endioxygruppe med formel (II) \ /°_ (II)
Pi'S- hvori 15 Rg og R7, som er ens eller forskellige, er hydrogen, lavere al kyl eller al kyl, som tilsammen danner en cyclopentyl- eller cyclohexylring.
Rj er især hydrogen eller al kyl med 1 til 4 carbonatomer såsom methyl, ethyl og isopropyl. I hele beskrivelsen betyder "alkyl" ligekædede og forgrenede alkylgrupper. Specifikke alkylgrupper for R2, 20 Rj, R4, Rg, Rg og Ry omfatter methyl, ethyl, isopropyl og n-propyl. Når X er CH2, kan R^ og Rg kombineres til dannelse af en benzenring, der er fusioneret til den 6-leddede, X-holdige ring, dvs. at R^ og Rg definerer al katrienylgruppen =CH-CH=CH-CH=.
En speciel gruppe forbindelser med formel (I) er sådanne, hvori X 25 er oxygen og både R2 og Rg og R^ og Rg tilsammen danner methylendioxy-grupper med formel (II), hvori Rg og Ry begge er hydrogen og al kyl eller tilsammen danner en spiro-cyclopentyl- eller cyclohexylring, især, når Rg og Ry begge er al kyl såsom methyl. En anden gruppe forbindelser er sådanne, hvori X er CH2 og R^ og Rg danner en benzenring. En tredje 30 gruppe forbindelser med formel (I) er sådanne, hvori både R2 og Rg er hydrogen.
Forbindelserne med formel (I) kan syntetiseres ved hjælp af følgende fremgangsmåde:
Omsætning af en alkohol med formlen RCHgOH, hvor R har formlen 35 (III) -O. (III) R, Rj
DK 165003 B
3 med sulfurylchlorid med formlen SOgCl^ i nærværelse af en base såsom triethylamin eller pyridin ved en temperatur på ca. -40 til 25°C i et opløsningsmiddel såsom diethylether eller methylenchlorid til dannelse af et chlorsulfat med formlen RCHgOSi^Cl.
5 Chlorsulfatet med formlen RCH20S02C1 kan dernæst omsættes med en amin med formlen RjNH2 ved en temperatur på ca. -40 til 25°C i et opløsningsmiddel såsom methylenchlorid eller acetonitril til dannelse af en forbindelse med formel (I). Omsætningsbetingelserne er også beskrevet af T. Tsuchiya, et al., i Tet. Letters, nr. 36, side 3365-3368 10 (1978).
Udgangsforbindelserne med formlen RCH20H kan fås kommercielt eller som kendt i teknikken. Eksempelvis kan udgangsforbindelser med formlen RCHgOH, hvori både R2 og Rg og R^ og Rg er identiske og har formlen (II), opnås ved fremgangsmåderne ifølge R.F. Brady i Carbohydrate 15 Research, bind 15, side 35-40 (1970), eller ved omsætning af trimethyl-silylenoletheren af en RgCORj-keton eller -aldehyd med fruktose ved en temperatur på ca. 25°C i et opløsningsmiddel såsom et halogencarbon, fx. methylenchlorid, i nærværelse af en protisk syre såsom saltsyre eller en Lewis-syre såsom zinkchlorid. Trimethylsilylenoletherreaktionen er be-20 skrevet af G. L. Larson et al i J. Org. Chem., bind 38, nr. 22, side 3935 (1973).
Desuden kan carboxylsyrer og aldehyder med formlen RCOOH og RCHO reduceres til forbindelser med formel RCHgOH ved standard-reduktionsteknikker, fx. omsætning med lithiumaluminiumhydrid, natriumborhydrid 25 eller boran-THF-kompleks i et inert opløsningsmiddel såsom dig!yme, THF eller toluen ved en temperatur fra ca. 0 til 100°C, fx. som beskrevet af H.O. House i "Modern Synthetic Reactions", 2. oplag, side 45-144 (1972).
Forbindelserne ifølge opfindelsen omfatter forskellige individuelle isomere samt racematerne deraf, fx. de forskellige forbindelser, hvori 30 R2, Rg> R^ og Rg er bundet i alfa- eller beta-stilling i forhold til den 6-leddede ring, dvs. under og over tegningens plan. Fortrinsvis er methylendioxygruppens (II) oxygener bundet på samme side af den 6-leddede ring.
Forbindelserne med formel (I) er nyttige som antikonvulsiviske 35 midler. Den antikonvulsiviske aktivitet af forbindelserne bestemtes under anvendelse af en standard "maksimal elektrochock-test" (MES). I denne test indikeres aktivitet ved en blokering af den toniske ekstensor-spasme, der frembringes ved påføring af et elektrisk chock til
DK 165003 B
4 mus via hornhindeelektroder som beskrevet af Swinyard, et al., i J.
Pharmacol. Exptl. Therap. 106, 319 (1952), og anføres som % blokering.
En nyere beskrivelse af nutidig antikonvulsivisk lægemiddel-screening kan findes i Swinyard, et al., Epilepsia 19, 409 (1978).
5 Den antikonvulsiviske aktivitet af forbindelser med formel (I), der testes iht. Swinyard-metoden (1952), vises i den følgende tabel (I):
Tabel (I) 10 Eksempel Forbindelse MES-test EDgg *(mg/kg, i.p.) 1 /-—o 195 / \-CH,OSO,NH, 15 CH, 2 ^ ^t-C8,0S0,NH, 270 O CH,OSO,NH, 20 3 ch‘^/^Vch* 26 cC° CH‘ _0 ch^so.hhch, 70% blok ved 200 mg/kg} i p 4 ch^*>^Vch‘ 25 CHj CH, - CH,OSO,NH, 5 O 55 30 ♦Medmindre andet er anført.
Til behandling af epilepsi kan der i et voksent gennemsnitsmenneske anvendes en forbindelse med formel (I) i en daglig dosering i området fra ca. 30 til 2000 mg, sædvanligvis i 2 til 4 doser.
35 En enhedsdosis indeholder ca. 10 til 500 mg aktiv bestanddel.
Almindeligvis kan forbindelser med formel (I) anvendes til behandling af epilepsi på en måde, der ligner den, der anvendes med phenytoin. Medicinske aspekter af behandlingen af epilepsi er 5 beskrevet af L.S. Goodman, et al., i "The Pharmacological Basis of Therapeutics", 5. oplag, s. 201-226, Macmillan (1975).
Desuden inhiberer forbindelser med formel (I) carbonsyreanhy-drase, som vist ved de af S.J. Dodgson. et al., i The Proc. Natl.
5 Acad. Sci., USA, 77, s. 5562-5566 (1980) eller af N. Itada, et al., i The Journal Biol. Chem., 252, s. 3881-3890 (1977) beskrevne fremgangsmåder og er som sådanne anvendelige til behandling af glaukom. Sammenhængen mellem behandling af glaukom og carbon-syreanhydrase-inhi bering er beskrevet af A. Stein, et al., i The 10 American Journal of Opthalmology, 95:222-228 (1983). Til behandling af glaukom kan en forbindelse med formel (I) administreres systemisk, fx. ad oral eller parenteral vej som beskrevet nedenfor, eller topisk i øjet som en mineralolieopløsning eller -suspension, eller vandig suspension. Når forbindelsen anvendes systemisk, administre-15 res den i en mængde fra ca. 50 til 500 mg per dag for et voksent gennemsnits-menneske, mens den topiske dosering er ca. 1 til 3 dråber (per øje) af en opløsning eller suspension, der indeholder ca. 1 til 5 vægt-% af en forbindelse med formel (I), idet dosen administreres ca. 1 til 4 gange daglig.
20 Den foreliggende opfindelse omfatter mellemprodukter med formlen rch2oso2ci.
I de følgende eksempler og i hele beskrivelsen anvendes følgende forkortelser: g (gram), ml (milliliter), cm (centimeter), v/v (volumen til volumen), smp. (smeltepunkt), TLC (tyndtlagskromatografi), NMR 25 (kernemagnetisk resonans), IR (infrarød), DMF (dimethylformamid), THF (tetrahydrofuran) og C, Η, N, etc. (de kemiske symboler for grundstofferne) .
Eksempel 1 30 (Tetrahydro-2H-pyran-2-ylImethansulfamat
Til en kold opløsning (-5°C) af tetrahydropyran-2-methanol (2,33 g, 0,02 mol) i DMF (40 ml) sattes 50% olieagtigt natriumhydrid (1,17 g, 0,024 mol som NaH). Efter omrøring i 45 minutter tilsattes sulfamoylchlorid (3,42 g, 0,03 mol) og omrøringen fortsattes i yder-35 ligere 45 minutter ved -5°C. Reaktionsblandingen hældtes i koldt vand og ekstraheredes med chloroform. Det organiske lag tørredes (Na2S0^) og opløsningsmidlerne fjernedes under vakuum, hvilke gav en sirup, der kromatograferedes på tør kolonne (der elueredes med ethyl acetat:hexan,
DK 165003 B
6 4:1 v/v), hvilket gav rent (tetrahydro-2H-pyran-2-yl)methansul famat som en svagt gul sirup, IR:(CHC13) 1180 cm"1 og 1370 cm"1 (0S02NH2).
Eksempel 2 5 (1-methylcyclohexyl Imethansulfamat
Til en kold opløsning (-4°C) af (1-methylcyclohexyl)methanol (6,2 g, 0,048 mol) i DMF (90 ml) sattes 50% olieagtigt natriumhydrid (82,81 g, 0,059 mol som NaH). Efter omrøring i 1 time tilsattes sulfamoylchlo-rid (7,82 g, 0,062 mol) og omrøringen fortsattes i yderligere 30 minut-10 ter ved -4°C. Reaktionsblandingen hældtes i koldt vand og ekstraheredes med toluen. Det organiske lag tørredes (Na^O^) og opløsningsmidlerne fjernedes under vakuum, hvilket gav en sirup, der krystalliserede efter afkøling. Omkrystallisation fra chloroform/ hexan gav rent (1-methyl-cyclohexyl)methansulfamat, smp. 40-42°C.
15
Eksempel 3 2,3:4,5-bi s-0-(1-methylethyl i den)-fl-D-fruktopyranosesulfamat
Til en kold opløsning (-4°C) af 2,3:4,5-di-0-isopropyliden-/l-fruktopyranose (75 g, 0,29 mol) i DMF (725 ml) sattes 50% olieagtigt 20 natriumhydrid (16,34 g, 0,34 mol som NaH). Efter omrøring i 90 minutter tilsattes sulfamoylchlorid (54,9 g, 0,48 mol) og omrøringen fortsattes i yderligere 3\ time ved denne temperatur. Reaktionsblandingen hældtes i koldt vand og ekstraheredes med toluen. Det organiske lag tørredes (Na2S04) og opløsningsmidlerne fjernedes 25 under vakuum, hvilket gav en sirup, som øjeblikkeligt krystalliserede. Omkrystall i sati on fra ethylacetat/hexan gav rent 2,3:4,5-bis--0-(l-methylethyliden)-j8-D-fruktopyranosesulfamat, smp. 125-126°C.
Eksempel 4 30 2,3:4,5-bi s-0-(1-methylethyl iden)-g-D-fruktopyranosemethylsul famat En opløsning af sulfonylchlorid (93 ml, 1,15 mol) i methylen-chlorid (100 ml) sattes dråbevis til en kold opløsning (-35°C) af 2,3:4,5-di-0-isopropyliden-/J-D-fruktopyranose (150 g, 0,58 mol) i methylenchlorid (400 ml) og pyridin (150 ml). Reaktionsblandingen 35 omrørtes og opvarmedes til stuetemperatur (25°C); den omrørtes i yderligere 2 timer. Opløsningsmidler fjernedes under vakuum. Det resulterende halvfaste stof opløstes i vandfri acetonitril (35 g, 150 ml) og methylamin bobledes igennem. Reaktionsbeholderen lukkedes tæt og
DK 165003 B
7 opløsningsmidler fjernedes under vakuum. Den resulterende sirup underkastedes væskekromatografi (tør kolonne ethyl acetat: hexan, 4:1), hvilket gav en lysegul sirup, 2,3:4,5-bis-0-(l-methylethyliden)-0-D-fruktopyranosemethylsul famat, som var homogent ifølge TLC og *H NHR.
5
Eksempel 5 (1,2,3,4-tetrahydro-2-naphthal enyl )methyl sul f amsyreester
Til en kold opløsning (-5°) af (l,2,3,4-tetrahydro-2-naphtha-lenyl)methanol (7,1 g, 0,044 mol) i DMF. (80 ml) sattes 50% olieagtigt 10 natriumhydrid (2,56 g, 0,054 mol som NaH). Efter omrøring i 45 minutter tilsattes sulfamoylchlorid (6,6 g, 0,057 mol) og omrøring fortsattes i yderligere 95 minutter ved -5°C. Reaktionsblandingen hældtes i koldt vand og ekstraheredes med toluen. Det organiske lag tørredes (NagSO^) og opløsningsmidlerne fjernedes under vakuum til dannelse af en 15 sirup, der øjeblikkeligt krystalliserede. Omkrystallisation fra chloro-form/hexan gav ren (l,2,3,4-tetrahydro-2-naphthalenyl)methylsulfamsyre-ester, smp. 108-109°C, som et hvidt fast stof.

Claims (3)

  1. 5 DK 165003B 8 Chlorsulfat med formlen RC^OSOgCl, hvor R har formlen (III): (IH)
  2. 10 R, R, 15 hvori R2, R3, R4 og Rg er, uafhængigt af hinanden, hydrogen eller lavere al kyl og, når X er CH2, er R4 og R5 eventuelt alkengrupper, der tilsammen danner en benzenring og, når X er oxygen, danner R2 og R3 og/eller R4 og Rg eventuelt en methyl endioxygruppe med formel (II)
  3. 20 Rfi ο χ / c r{ no- (II) hvori Rø og R^, som er ens eller forskellige, er hydrogen, lavere al kyl, 25 eller al kyl, som tilsammen danner en cyclopentyl- eller cyclohexylring. 30 35
DK198191A 1983-09-26 1991-12-09 Chlorsulfat DK165003C (da)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US53547583 1983-09-26
US06/535,475 US4513006A (en) 1983-09-26 1983-09-26 Anticonvulsant sulfamate derivatives

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DK198191D0 DK198191D0 (da) 1991-12-09
DK198191A DK198191A (da) 1991-12-09
DK165003B true DK165003B (da) 1992-09-28
DK165003C DK165003C (da) 1993-02-08

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DK457784A DK165004C (da) 1983-09-26 1984-09-25 Sulfamatderivater og farmaceutiske praeparater indeholdende disse
DK198191A DK165003C (da) 1983-09-26 1991-12-09 Chlorsulfat
DK199101982A DK173923B1 (da) 1983-09-26 1991-12-09 Azidosulfat

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DK457784A DK165004C (da) 1983-09-26 1984-09-25 Sulfamatderivater og farmaceutiske praeparater indeholdende disse

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DK199101982A DK173923B1 (da) 1983-09-26 1991-12-09 Azidosulfat

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JP (2) JPS60109558A (da)
KR (1) KR920001775B1 (da)
AT (1) ATE36149T1 (da)
AU (1) AU564842B2 (da)
CA (1) CA1241951A (da)
DE (1) DE3473143D1 (da)
DK (3) DK165004C (da)
ES (1) ES8602634A1 (da)
FI (1) FI79095C (da)
HU (1) HU194540B (da)
IE (1) IE57684B1 (da)
MX (1) MX9202630A (da)
NL (1) NL990025I2 (da)
NO (2) NO170280C (da)
NZ (1) NZ209494A (da)
ZA (1) ZA847550B (da)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4792569A (en) * 1987-08-27 1988-12-20 Mcneilab, Inc. Anticonvulsant phenethyl sulfamates
US5273993A (en) * 1989-06-12 1993-12-28 A. H. Robins Company, Incorporated Compounds having one or more aminosulfonyloxy radicals useful as pharmaceuticals
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