CA1157859A - Derives de decaprenylamines - Google Patents

Derives de decaprenylamines

Info

Publication number: CA1157859A
Authority: CA; Canada
Prior art keywords: decaprenyl; process according; formula; iii; group
Prior art date: 1980-11-21
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.): Expired

Application number

CA000365241A

Other languages

English (en)

Inventor

Yoshiyuki Tahara

Hiroyasu Koyama

Reiko Kubota

Yasuhiro Komatsu

Toshihiro Takahashi

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Nisshin Seifun Group Inc

Original Assignee

Nisshin Seifun Group Inc

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.)

1980-11-21

Filing date

1980-11-21

Publication date

1983-11-29

1980-11-21 Application filed by Nisshin Seifun Group Inc filed Critical Nisshin Seifun Group Inc

1980-11-21 Priority to CA000365241A priority Critical patent/CA1157859A/fr

1983-11-29 Application granted granted Critical

1983-11-29 Publication of CA1157859A publication Critical patent/CA1157859A/fr

Status Expired legal-status Critical Current

Links

AFMZGMJNKXOLEM-JXMROGBWSA-N (2e)-3,7-dimethylocta-2,6-dien-1-amine Chemical class CC(C)=CCC\C(C)=C\CN AFMZGMJNKXOLEM-JXMROGBWSA-N 0.000 title claims abstract description 7
239000002253 acid Substances 0.000 claims abstract description 17
150000003839 salts Chemical class 0.000 claims abstract description 17
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 15
150000002391 heterocyclic compounds Chemical class 0.000 claims abstract description 10
125000005842 heteroatom Chemical group 0.000 claims abstract description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 8
RORDEOUGMCQERP-UHFFFAOYSA-N (2Z,6Z,10Z,14Z,18Z,22Z,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyl-tetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-ol Natural products CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCO RORDEOUGMCQERP-UHFFFAOYSA-N 0.000 claims abstract description 4
RORDEOUGMCQERP-CMVHWAPMSA-N (2e,6e,10e,14e,18e,22e,26e,30e,34e)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-ol Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CO RORDEOUGMCQERP-CMVHWAPMSA-N 0.000 claims abstract description 4
125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 4
125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
239000001301 oxygen Substances 0.000 claims abstract description 4
229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
239000011593 sulfur Substances 0.000 claims abstract description 4
150000004820 halides Chemical class 0.000 claims abstract description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims abstract description 3
150000003459 sulfonic acid esters Chemical class 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 30
238000002360 preparation method Methods 0.000 claims description 18
239000000126 substance Substances 0.000 claims description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 2
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 5
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims 1
241000251539 Vertebrata <Metazoa> Species 0.000 abstract description 5
230000009385 viral infection Effects 0.000 abstract description 2
150000001875 compounds Chemical class 0.000 description 16
239000000243 solution Substances 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
102000014150 Interferons Human genes 0.000 description 10
108010050904 Interferons Proteins 0.000 description 10
241000699670 Mus sp. Species 0.000 description 10
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239000002775 capsule Substances 0.000 description 9
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CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
241000700605 Viruses Species 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
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235000019441 ethanol Nutrition 0.000 description 4
239000000411 inducer Substances 0.000 description 4
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239000007788 liquid Substances 0.000 description 4
VOVZXURTCKPRDQ-CQSZACIVSA-N n-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-5-(1h-pyrazol-5-yl)pyridine-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=NC=C(C(=O)NC=2C=CC(OC(F)(F)Cl)=CC=2)C=C1C1=CC=NN1 VOVZXURTCKPRDQ-CQSZACIVSA-N 0.000 description 4
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000003443 antiviral agent Substances 0.000 description 3
239000003795 chemical substances by application Substances 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
230000001939 inductive effect Effects 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
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JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
HFGHRUCCKVYFKL-UHFFFAOYSA-N 4-ethoxy-2-piperazin-1-yl-7-pyridin-4-yl-5h-pyrimido[5,4-b]indole Chemical compound C1=C2NC=3C(OCC)=NC(N4CCNCC4)=NC=3C2=CC=C1C1=CC=NC=C1 HFGHRUCCKVYFKL-UHFFFAOYSA-N 0.000 description 2
CBQYNPHHHJTCJS-UHFFFAOYSA-N Alline Chemical compound C1=CC=C2C3(O)CCN(C)C3NC2=C1 CBQYNPHHHJTCJS-UHFFFAOYSA-N 0.000 description 2
235000017060 Arachis glabrata Nutrition 0.000 description 2
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VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
102000003886 Glycoproteins Human genes 0.000 description 2
108090000288 Glycoproteins Proteins 0.000 description 2
101000911019 Homo sapiens Zinc finger protein castor homolog 1 Proteins 0.000 description 2
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
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239000004698 Polyethylene Substances 0.000 description 2
235000004443 Ricinus communis Nutrition 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
241000700618 Vaccinia virus Species 0.000 description 2
102100026655 Zinc finger protein castor homolog 1 Human genes 0.000 description 2
239000000654 additive Substances 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
238000004500 asepsis Methods 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
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235000019438 castor oil Nutrition 0.000 description 2
239000003240 coconut oil Substances 0.000 description 2
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235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
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208000015181 infectious disease Diseases 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
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AILFRWRYZZVJTL-UHFFFAOYSA-N 1-methylpiperazin-1-ium;chloride;hydrochloride Chemical compound Cl.Cl.CN1CCNCC1 AILFRWRYZZVJTL-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 1
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WOLHOYHSEKDWQH-UHFFFAOYSA-N amantadine hydrochloride Chemical compound [Cl-].C1C(C2)CC3CC2CC1([NH3+])C3 WOLHOYHSEKDWQH-UHFFFAOYSA-N 0.000 description 1
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IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
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JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000365241A 1980-11-21 1980-11-21 Derives de decaprenylamines Expired CA1157859A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000365241A CA1157859A (fr)	1980-11-21	1980-11-21	Derives de decaprenylamines

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000365241A CA1157859A (fr)	1980-11-21	1980-11-21	Derives de decaprenylamines

Publications (1)

Publication Number	Publication Date
CA1157859A true CA1157859A (fr)	1983-11-29

Family

ID=4118520

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000365241A Expired CA1157859A (fr)	1980-11-21	1980-11-21	Derives de decaprenylamines

Country Status (1)

Country	Link
CA (1)	CA1157859A (fr)

1980
- 1980-11-21 CA CA000365241A patent/CA1157859A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2000-11-29	MKEX	Expiry

Publication	Publication Date	Title
TWI245770B (en)	2005-12-21	Calcium (3s) tetrahydro-3-furanyl(1s,2r)-3-[[(4-aminophenyl)sulfonyl](isobutyl)amino]-1-benzyl-2-(phosphonooxy)propylcarbamate
CA1055396A (fr)	1979-05-29	Compose pour le traitement des arythmies cardiaques
US4340760A (en)	1982-07-20	Monophenylamine derivatives
EP0104614B1 (fr)	1986-12-30	Dérivés du phénylpipérazine et leur procédé de préparation
CA1297033C (fr)	1992-03-10	Utilisation d'amides de l'acide carboxylique pour traiter les inflammations
US2789110A (en)	1957-04-16	Amino alcohols substituted by bicycloalkyl residues and a process of making same
TW200407310A (en)	2004-05-16	Compounds
JPS6242905B2 (fr)	1987-09-10
US4658063A (en)	1987-04-14	Isoprenylamine derivatives
CA1172265A (fr)	1984-08-07	Derives de la nonaprenylamine
CA1183136A (fr)	1985-02-26	Derives de nonaprenylamine
US3789125A (en)	1974-01-29	Pharmaceutical compositions containing halo-substituted 2-amino-benzylamine-amides
US4265910A (en)	1981-05-05	Isoprenylamines
US4568765A (en)	1986-02-04	Isoprenylamine derivatives
US4393209A (en)	1983-07-12	Decaprenylamine derivatives
GB2065111A (en)	1981-06-24	Decaprenylamine derivatives
CA1133913A (fr)	1982-10-19	N-(1-methyl-2-pyrrolidinyl-methyl)-2,3-dimethoxy-5- methylsulfamoyl benzamide et ses derives; leurs methodes de preparation, et leur utilisation dans le traitement de troubles de l'appareil urinaire inferieur
CA1155459A (fr)	1983-10-18	Derives de decaprenylamine
CA1150268A (fr)	1983-07-19	Derives de la decaprenylamine
US4380668A (en)	1983-04-19	Decaprenylamine derivatives
US4431811A (en)	1984-02-14	Decaprenylamine derivatives
GB2065110A (en)	1981-06-24	Decaprenylamine Derivatives
WO1992007819A1 (fr)	1992-05-14	Derive de tri(alcoxy inferieur)benzene
GB2108105A (en)	1983-05-11	Polyisoprenylamine derivatives
US3821380A (en)	1974-06-28	2-alkylthio-4,6-diamino-5-pyrimidinesulfonamides as anti-hypertensives