PL117354B1 - Process for preparing novel derivatives of carboxylic acidst - Google Patents

Process for preparing novel derivatives of carboxylic acidst Download PDF

Info

Publication number: PL117354B1
Authority: PL; Poland
Prior art keywords: acid; formula; free; pyrrolinyl; salts
Prior art date: 1969-03-18

Application number

PL18515870A

Other languages

English (en)

Polish (pl)

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.)

1969-03-18

Filing date

1970-03-16

Publication date

1981-07-31

1970-03-16 Application filed filed Critical

1981-07-31 Publication of PL117354B1 publication Critical patent/PL117354B1/pl

Links

238000004519 manufacturing process Methods 0.000 title description 2
239000002253 acid Substances 0.000 claims description 32
150000003839 salts Chemical class 0.000 claims description 32
150000001875 compounds Chemical class 0.000 claims description 29
239000000203 mixture Substances 0.000 claims description 17
238000000034 method Methods 0.000 claims description 15
238000002360 preparation method Methods 0.000 claims description 12
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 10
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 9
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
125000005907 alkyl ester group Chemical group 0.000 claims description 7
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 6
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
150000001340 alkali metals Chemical class 0.000 claims description 5
239000001569 carbon dioxide Substances 0.000 claims description 5
229910002092 carbon dioxide Inorganic materials 0.000 claims description 5
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 5
235000019253 formic acid Nutrition 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
239000011777 magnesium Substances 0.000 claims description 5
229910052749 magnesium Inorganic materials 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
-1 pyrrolinylphenylmethyl residue Chemical group 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
150000007513 acids Chemical class 0.000 description 8
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125000000217 alkyl group Chemical group 0.000 description 5
230000003110 anti-inflammatory effect Effects 0.000 description 5
150000004820 halides Chemical class 0.000 description 5
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239000002184 metal Substances 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
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239000011574 phosphorus Substances 0.000 description 5
241000700159 Rattus Species 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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239000000825 pharmaceutical preparation Substances 0.000 description 3
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239000007858 starting material Substances 0.000 description 3
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BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
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DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000013543 active substance Substances 0.000 description 2
239000003513 alkali Substances 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
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239000001768 carboxy methyl cellulose Substances 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
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239000000679 carrageenan Substances 0.000 description 2
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239000003085 diluting agent Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
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230000002140 halogenating effect Effects 0.000 description 2
210000000548 hind-foot Anatomy 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
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239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000758 substrate Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
150000003556 thioamides Chemical class 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 2
BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
CSEWAUGPAQPMDC-UHFFFAOYSA-N 2-(4-aminophenyl)acetic acid Chemical compound NC1=CC=C(CC(O)=O)C=C1 CSEWAUGPAQPMDC-UHFFFAOYSA-N 0.000 description 1
BINHMKFDOKTOMX-UHFFFAOYSA-N 2-[4-(3,6-dihydro-2H-pyridin-1-yl)phenyl]acetic acid Chemical compound N1(CC=CCC1)C1=CC=C(C=C1)CC(=O)O BINHMKFDOKTOMX-UHFFFAOYSA-N 0.000 description 1
JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical compound C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 description 1
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
125000005274 4-hydroxybenzoic acid group Chemical group 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
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239000004215 Carbon black (E152) Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical class C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
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150000004767 nitrides Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 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
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
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239000003960 organic solvent Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
150000002926 oxygen Chemical class 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
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229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
125000001422 pyrrolinyl group Chemical group 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
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
229940100486 rice starch Drugs 0.000 description 1
239000000523 sample Substances 0.000 description 1
230000001235 sensitizing effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
229940032147 starch Drugs 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
230000007704 transition Effects 0.000 description 1
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrrole Compounds (AREA)

PL18515870A 1969-03-18 1970-03-16 Process for preparing novel derivatives of carboxylic acidst PL117354B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US80834369A	1969-03-18	1969-03-18

Publications (1)

Publication Number	Publication Date
PL117354B1 true PL117354B1 (en)	1981-07-31

Family

ID=25198519

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PL18515870A PL117354B1 (en)	1969-03-18	1970-03-16	Process for preparing novel derivatives of carboxylic acidst

Country Status (2)

Country	Link
CS (1)	CS181685B2 (cs)
PL (1)	PL117354B1 (cs)

1970
- 1970-03-16 PL PL18515870A patent/PL117354B1/pl unknown
- 1970-03-18 CS CS459470A patent/CS181685B2/cs unknown

Also Published As

Publication number	Publication date
CS181685B2 (en)	1978-03-31

Publication	Publication Date	Title
CH616921A5 (cs)	1980-04-30
US3729508A (en)	1973-04-24	Sulfonylbenzoic acids
FI82450C (fi)	1991-03-11	Foerfarande foer framstaellning av terapeutiskt anvaendbara difenyl- och fenylpyridylderivat.
EP0005231B1 (de)	1982-12-15	Isochinolinderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen
EP0005559B1 (de)	1981-11-04	Phenylaminothiophenessigsäuren, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
DD142545A5 (de)	1980-07-02	Verfahren zur herstellung neuer omega thiobutyramide
EP0001601A1 (en)	1979-05-02	Lactam compounds and methods for their preparation
CH574921A5 (en)	1976-04-30	Anti-inflammatory alpha-aminophenyl carboxylic acids
US3953461A (en)	1976-04-27	Amino derivatives of thiazolo[5,4-b]pyridine-6-carboxylic acids and esters
DE2811312A1 (de)	1979-09-27	Neue isochinolinderivate, verfahren zu ihrer herstellung und ihre verwendung zur herstellung von arzneimitteln
KR900004694B1 (ko)	1990-07-02	신규 α-아릴-α-피리딜 알카노인산 유도체의 제조방법
CS216206B2 (en)	1982-10-29	Method of making the derivatives of the diphenylpyrazole
PL138474B1 (en)	1986-09-30	Method of obtaining 2-hydromethyl-6-methyl-4-p-tolilo-4,5,6,7-tetrahydro-thieno(2,3-c)-pyridine
US3950539A (en)	1976-04-13	Substituted diaminoguanidines
US3875176A (en)	1975-04-01	2-benzoyl -3-amino-pyridines
US3825533A (en)	1974-07-23	N-carboxymethyl-n-substituted glycinate esters of 3-hydroxy-1,4-benzo-diazepin-2-ones
US3705920A (en)	1972-12-12	Sulfonylphenylphosphonic acids
PL116504B1 (en)	1981-06-30	Process for preparing novel derivatives of carboxylic acids
PL116539B1 (en)	1981-06-30	Process for preparing novel derivatives of carboxylic acids
GB1598628A (en)	1981-09-23	Guanidine derivatives
PL116495B1 (en)	1981-06-30	Process for preparing novel derivatives of carboxylic acids
US4012397A (en)	1977-03-15	2-Benzoyl-3-amino-pyridines
CH628045A5 (en)	1982-02-15	Process for the preparation of dibenzothiophene derivatives
US3969361A (en)	1976-07-13	2-Benzoyl-3-amino-pyridines
US4795758A (en)	1989-01-03	5-[2-(pyrrolidin-1-yl)ethoxy]-p-cymene derivatives, the process for the preparation of the said derivatives and drugs in which the said derivatives are present