IL27605A - Racemic and optically active 6h,7h-cis-7-amino-desacetyl-cephalosporanic acid derivatives and process of preparation - Google Patents

Racemic and optically active 6h,7h-cis-7-amino-desacetyl-cephalosporanic acid derivatives and process of preparation

Info

Publication number: IL27605A
Authority: IL; Israel
Prior art keywords: acid; group; compound; medium; derivative
Prior art date: 1966-03-15

Application number

IL6727605A

Other languages

English (en)

Original Assignee

Roussel Uclaf

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.)

1966-03-15

Filing date

1967-03-14

Publication date

1972-11-28

1967-03-14 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1972-11-28 Publication of IL27605A publication Critical patent/IL27605A/en

Links

238000000034 method Methods 0.000 title claims description 16
238000002360 preparation method Methods 0.000 title description 14
239000002253 acid Substances 0.000 claims description 30
150000001875 compounds Chemical class 0.000 claims description 25
239000000203 mixture Substances 0.000 claims description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
150000001718 carbodiimides Chemical class 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 3
150000001408 amides Chemical group 0.000 claims description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
150000003512 tertiary amines Chemical class 0.000 claims description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims 2
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
AVGQTJUPLKNPQP-UHFFFAOYSA-N 1,1,1-trichloropropane Chemical compound CCC(Cl)(Cl)Cl AVGQTJUPLKNPQP-UHFFFAOYSA-N 0.000 claims 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
230000002378 acidificating effect Effects 0.000 claims 1
RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims 1
229910000071 diazene Inorganic materials 0.000 claims 1
239000002184 metal Substances 0.000 claims 1
229940050176 methyl chloride Drugs 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
238000002844 melting Methods 0.000 description 14
230000008018 melting Effects 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
150000002596 lactones Chemical class 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 7
239000000047 product Substances 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
230000009102 absorption Effects 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 4
239000002609 medium Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000003242 anti bacterial agent Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 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
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical compound NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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 2
229940088710 antibiotic agent Drugs 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000010586 diagram Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
150000003141 primary amines Chemical group 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
235000002906 tartaric acid Nutrition 0.000 description 2
239000011975 tartaric acid Substances 0.000 description 2
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
229930186147 Cephalosporin Natural products 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241001658031 Eris Species 0.000 description 1
235000014443 Pyrus communis Nutrition 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000003466 anti-cipated effect Effects 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
244000052616 bacterial pathogen Species 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 1
229940124587 cephalosporin Drugs 0.000 description 1
150000001780 cephalosporins Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
GGWBHVILAJZWKJ-UHFFFAOYSA-N dimethyl-[[5-[2-[[1-(methylamino)-2-nitroethenyl]amino]ethylsulfanylmethyl]furan-2-yl]methyl]azanium;chloride Chemical compound Cl.[O-][N+](=O)C=C(NC)NCCSCC1=CC=C(CN(C)C)O1 GGWBHVILAJZWKJ-UHFFFAOYSA-N 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
125000005544 phthalimido group Chemical group 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
VDZXAOBGHPKGCS-UHFFFAOYSA-M sodium;1,4-dioxane;hydroxide Chemical compound [OH-].[Na+].C1COCCO1 VDZXAOBGHPKGCS-UHFFFAOYSA-M 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cephalosporin Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

IL6727605A 1966-03-15 1967-03-14 Racemic and optically active 6h,7h-cis-7-amino-desacetyl-cephalosporanic acid derivatives and process of preparation IL27605A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR53488A FR1492854A (fr)	1966-03-15	1966-03-15	Nouveaux dérivés de l'acide céphalosporanique et procédé de préparation
FR78320A FR91765E (fr)	1966-03-15	1966-09-30	Nouveaux dérivés de l'acide céphalosporanique et procédé de préparation

Publications (1)

Publication Number	Publication Date
IL27605A true IL27605A (en)	1972-11-28

Family

ID=26169221

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
IL37410A IL37410A (en)	1966-03-15	1967-03-14	Gamma-lactones of 2h-1,3-thiazine-4-carboxylic acid
IL6727605A IL27605A (en)	1966-03-15	1967-03-14	Racemic and optically active 6h,7h-cis-7-amino-desacetyl-cephalosporanic acid derivatives and process of preparation

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
IL37410A IL37410A (en)	1966-03-15	1967-03-14	Gamma-lactones of 2h-1,3-thiazine-4-carboxylic acid

Country Status (8)

Country	Link
US (1)	US3642788A (fr)
CH (1)	CH485772A (fr)
DE (1)	DE1695623C3 (fr)
DK (1)	DK129416B (fr)
FR (2)	FR1492854A (fr)
GB (1)	GB1156854A (fr)
IL (2)	IL37410A (fr)
NL (1)	NL6703896A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3905965A (en) *	1969-10-17	1975-09-16	Roussel Uclaf	Process of total synthesis of cephalosporin derivatives and intermediates
CN104130271A (zh) *	2014-08-18	2014-11-05	哈药集团制药总厂	一种头孢曲松内酯的合成方法
CN116655657A (zh) *	2023-05-31	2023-08-29	阜阳欣奕华制药科技有限公司	头孢呋辛杂质h的制备方法

1966
- 1966-03-15 FR FR53488A patent/FR1492854A/fr not_active Expired
- 1966-09-30 FR FR78320A patent/FR91765E/fr not_active Expired
1967
- 1967-03-13 US US622440A patent/US3642788A/en not_active Expired - Lifetime
- 1967-03-14 IL IL37410A patent/IL37410A/en unknown
- 1967-03-14 CH CH369467A patent/CH485772A/fr not_active IP Right Cessation
- 1967-03-14 IL IL6727605A patent/IL27605A/en unknown
- 1967-03-14 DK DK131467AA patent/DK129416B/da not_active IP Right Cessation
- 1967-03-15 DE DE1695623A patent/DE1695623C3/de not_active Expired
- 1967-03-15 NL NL6703896A patent/NL6703896A/xx unknown
- 1967-03-15 GB GB12149/67A patent/GB1156854A/en not_active Expired

Also Published As

Publication number	Publication date
DE1695623A1 (de)	1971-04-22
CH485772A (fr)	1970-02-15
FR1492854A (fr)	1967-08-25
GB1156854A (en)	1969-07-02
NL6703896A (fr)	1967-09-18
DK129416B (da)	1974-10-07
DE1695623C3 (de)	1978-06-01
IL37410A (en)	1972-05-30
US3642788A (en)	1972-02-15
DK129416C (fr)	1975-03-17
FR91765E (fr)	1968-08-09
DE1695623B2 (de)	1977-10-13

Publication	Publication Date	Title
JPS61251650A (ja)	1986-11-08	（ｚ）−１−フエニル−１−ジエチルアミノカルボニル−２−アミノメチルシクロプロパン塩酸塩の製造方法
SU474980A3 (ru)	1975-06-25	Способ получени (1-п-хлорбензоил-5-метокси-2-метил-3-индол) ацетоксиуксусной кислоты или ее солей
NO146202B (no)	1982-05-10	Fremgangsmaate for omleiring av et 6-acylamidopenicillansyresulfoksyd til en 7-acylamido-3-metylceph-3-em-4-karboksylsyre
FI73968C (fi)	1987-12-10	Foerfarande foer framstaellning av fenylglycylkloridhydroklorider.
SU458131A3 (ru)	1975-01-25	Способ получени шифровых оснований 7-амино-3-дезацфетоксицефалоспорановой кислоты
IL27605A (en)	1972-11-28	Racemic and optically active 6h,7h-cis-7-amino-desacetyl-cephalosporanic acid derivatives and process of preparation
SU645581A3 (ru)	1979-01-30	Способ получени -2-галоид-6- метил-8-цианометил или -2-галоид6-метил-8-карбоксамидометилэрголинов
US4193918A (en)	1980-03-18	Process for the preparation of hydroxy-alpha-amino-benzyl penicillin
US3901891A (en)	1975-08-26	13-bromolysergic acid compounds
US3428639A (en)	1969-02-18	Preparation of ergot alkaloids
NO137999B (no)	1978-02-27	Analogifremgangsm}te ved fremstilling av terapeutisk aktive oxofurylestere av 6-(alfa-aminofenylacetamido)-penicillansyre
SU528878A3 (ru)	1976-09-15	Способ получени производных (гетероарилметил)-дезоксинорморфина или- дезоксиноркодеина, или их солей
US3860607A (en)	1975-01-14	Process for preparing hydroxy-l-proline or n-acetyl-hydroxy-l-proline from hydrolyzed gelatin
US2763652A (en)	1956-09-18	Piperazinediones and methods for their preparation
US3825531A (en)	1974-07-23	Process for producing penicillin derivatives
KR830001969B1 (ko)	1983-09-29	6―｛D―(―) α-(4―에틸-2. 3-디옥소-1 피페라지노카보닐아미노) 페닐(또는 하이드록시페닐)아세트아미도 페니실란산 및 그 염의 제조방법
US4123611A (en)	1978-10-31	N-protected amino compounds
US3022309A (en)	1962-02-20	Berbine derivatives
SU735169A3 (ru)	1980-05-15	Способ получени производных цефалоспорина
JPH06104670B2 (ja)	1994-12-21	化学化合物の新規製法
SU420175A3 (fr)	1974-03-15
US3047578A (en)	1962-07-31	Substituted reserpine and process of making the same
SU584781A3 (ru)	1977-12-15	Способ получени производных 1-ацилгомопиримидазола или их солей
US4179557A (en)	1979-12-18	Acylation of 7-aminocephalosporanic acids
US3120531A (en)	1964-02-04	10-bromoyohimbine alkaloids