DK142698B - Fremgangsmåde til fremstilling af fritstrømmende krystaller af tris (hydroxymethyl) aminomethan-saltet af prostaglandin E2 eller F2alfa. - Google Patents

Fremgangsmåde til fremstilling af fritstrømmende krystaller af tris (hydroxymethyl) aminomethan-saltet af prostaglandin E2 eller F2alfa. Download PDF

Info

Publication number: DK142698B
Authority: DK; Denmark
Prior art keywords: tris; hydroxymethyl; acetonitrile; free; prostaglandin
Prior art date: 1970-06-01

Application number

DK263771AA

Other languages

Danish (da)

English (en)

Other versions

DK142698C (fr

Inventor

Walter Morozowich

Original Assignee

Upjohn Co

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.)

1970-06-01

Filing date

1971-05-28

Publication date

1980-12-22

1971-05-28 Application filed by Upjohn Co filed Critical Upjohn Co

1972-08-14 Priority to DK400972A priority Critical patent/DK142724B/da

1972-08-14 Priority to DK401072A priority patent/DK133539B/da

1980-12-22 Publication of DK142698B publication Critical patent/DK142698B/da

1981-08-24 Application granted granted Critical

1981-08-24 Publication of DK142698C publication Critical patent/DK142698C/da

Links

239000013078 crystal Substances 0.000 title description 17
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 title description 15
XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 title description 12
229960002986 dinoprostone Drugs 0.000 title description 12
XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 title description 12
238000000034 method Methods 0.000 title description 5
238000002360 preparation method Methods 0.000 title description 5
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 69
239000000243 solution Substances 0.000 description 21
150000003839 salts Chemical class 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
239000000203 mixture Substances 0.000 description 10
150000003180 prostaglandins Chemical class 0.000 description 10
PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
239000011521 glass Substances 0.000 description 6
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
239000000047 product Substances 0.000 description 5
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
239000007983 Tris buffer Substances 0.000 description 4
239000002585 base Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
238000003756 stirring Methods 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000001802 infusion Methods 0.000 description 3
239000000644 isotonic solution Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
238000002156 mixing Methods 0.000 description 3
229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
-1 amine salts Chemical class 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
230000033228 biological regulation Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
238000010253 intravenous injection Methods 0.000 description 2
230000002175 menstrual effect Effects 0.000 description 2
WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
206010000234 Abortion spontaneous Diseases 0.000 description 1
101000692466 Bos taurus Prostaglandin F synthase 2 Proteins 0.000 description 1
206010000210 abortion Diseases 0.000 description 1
231100000176 abortion Toxicity 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
CAJZGSNKLFFARL-UHFFFAOYSA-N aminooxymethanol Chemical compound NOCO CAJZGSNKLFFARL-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000000498 cooling water Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000011010 flushing procedure Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
230000006698 induction Effects 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
208000015994 miscarriage Diseases 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229940094443 oxytocics prostaglandins Drugs 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
208000000995 spontaneous abortion Diseases 0.000 description 1
239000002699 waste material Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/46—Unsaturated compounds containing hydroxy or O-metal groups containing rings other than six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DK263771AA 1970-06-01 1971-05-28 Fremgangsmåde til fremstilling af fritstrømmende krystaller af tris (hydroxymethyl) aminomethan-saltet af prostaglandin E2 eller F2alfa. DK142698B (da)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
DK400972A DK142724B (da)	1970-06-01	1972-08-14	Fremgangsmåde til fremstilling af fritstrømmende krystaller af tris (hydroxymethyl)aminomethan-saltet af prostaglandin E2.
DK401072A DK133539B (da)	1970-06-01	1972-08-14	Middel til regulering af pattedyrs reproduktive cyclus.

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US4245870A	1970-06-01	1970-06-01
US4245870		1970-06-01

Publications (2)

Publication Number	Publication Date
DK142698B true DK142698B (da)	1980-12-22
DK142698C DK142698C (fr)	1981-08-24

Family

ID=21922041

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK263771AA DK142698B (da)	1970-06-01	1971-05-28	Fremgangsmåde til fremstilling af fritstrømmende krystaller af tris (hydroxymethyl) aminomethan-saltet af prostaglandin E2 eller F2alfa.

Country Status (20)

Country	Link
US (1)	US3657327A (fr)
JP (1)	JPS5523825B1 (fr)
BE (1)	BE767926A (fr)
CH (2)	CH563329A5 (fr)
DE (1)	DE2126127C2 (fr)
DK (1)	DK142698B (fr)
ES (1)	ES391759A1 (fr)
FI (1)	FI53308C (fr)
FR (1)	FR2100712B1 (fr)
GB (1)	GB1288174A (fr)
GT (1)	GT197129402A (fr)
IL (1)	IL36860A (fr)
NL (1)	NL7107062A (fr)
NO (2)	NO132194C (fr)
OA (1)	OA03734A (fr)
PH (1)	PH9218A (fr)
PL (1)	PL81549B1 (fr)
SE (3)	SE387340B (fr)
SU (1)	SU384228A3 (fr)
ZA (1)	ZA713181B (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3888916A (en) *	1974-08-01	1975-06-10	Upjohn Co	Amantadine salt of 16,16-dimethyl-pge' 2
HU185926B (en) *	1979-09-27	1985-04-28	Agostne Kahan	Process for preparing water soluble derivatives of non-steroid antiinflammatory compositions and pharmaceutical compositins containing such derivatives
ZA815504B (en) *	1980-09-15	1982-08-25	Upjohn Co	Crystalline pgi2 methyl ester
US4912235A (en) *	1983-12-22	1990-03-27	Syntex (U.S.A.) Inc.	Processes and intermediates for making 16-phenoxy- and 16-substituted phenoxy-prostatrienoic acid derivatives and their stereoisomers
US4804787A (en) *	1983-12-22	1989-02-14	Syntex (U.S.A.) Inc.	Processes and intermediates for making 16-phenoxy and 16-substituted phenoxy-prostatrienoic acid derivatives
US6103765A (en)	1997-07-09	2000-08-15	Androsolutions, Inc.	Methods for treating male erectile dysfunction
CA2295595A1 (fr)	1997-07-09	1999-01-21	Androsolutions, Inc.	Compositions et procedes perfectionnes de traitement des troubles de l'erection chez l'homme
DK2370440T3 (en) *	2008-12-08	2014-12-08	Glaxosmithkline Llc	8-Chloro-3-pentyl-3,7-dihydro-1H-purine-2,6-dion2-amino-2- (hydroxymethyl) -1,3-propandiolanhydrat for the treatment of diseases
CN106810484B (zh) *	2016-12-28	2019-04-12	宁波第二激素厂	氨基丁三醇前列腺素F2α的合成方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3069322A (en) *	1958-05-28	1962-12-18	Bergstrom Sune	Pge and pgf

1970
- 1970-06-01 US US42458A patent/US3657327A/en not_active Expired - Lifetime
1971
- 1971-05-14 GT GT197129402A patent/GT197129402A/es unknown
- 1971-05-14 IL IL36860A patent/IL36860A/xx unknown
- 1971-05-17 GB GB1521171A patent/GB1288174A/en not_active Expired
- 1971-05-17 ZA ZA713181A patent/ZA713181B/xx unknown
- 1971-05-24 NL NL7107062A patent/NL7107062A/xx unknown
- 1971-05-26 DE DE2126127A patent/DE2126127C2/de not_active Expired
- 1971-05-28 DK DK263771AA patent/DK142698B/da not_active IP Right Cessation
- 1971-05-28 SE SE7402845A patent/SE387340B/xx unknown
- 1971-05-28 FI FI1499/71A patent/FI53308C/fi active
- 1971-05-28 SE SE7106934A patent/SE377459B/xx unknown
- 1971-05-28 FR FR7119658A patent/FR2100712B1/fr not_active Expired
- 1971-05-28 OA OA54263A patent/OA03734A/fr unknown
- 1971-05-28 NO NO2017/71A patent/NO132194C/no unknown
- 1971-05-31 ES ES391759A patent/ES391759A1/es not_active Expired
- 1971-05-31 SU SU1664093A patent/SU384228A3/ru active
- 1971-05-31 PL PL1971148507A patent/PL81549B1/pl unknown
- 1971-06-01 BE BE767926A patent/BE767926A/fr not_active IP Right Cessation
- 1971-06-01 JP JP3756871A patent/JPS5523825B1/ja active Pending
- 1971-06-01 CH CH800071A patent/CH563329A5/xx not_active IP Right Cessation
- 1971-06-01 CH CH366475A patent/CH563330A5/xx not_active IP Right Cessation
1972
- 1972-06-13 NO NO2082/72A patent/NO142499C/no unknown
1973
- 1973-05-07 PH PH14398*UA patent/PH9218A/en unknown
1974
- 1974-03-04 SE SE7402846A patent/SE411345B/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK142698C (fr)	1981-08-24
NO132194B (fr)	1975-06-23
ZA713181B (en)	1972-02-23
FI53308C (fi)	1978-04-10
CH563329A5 (fr)	1975-06-30
PL81549B1 (fr)	1975-08-30
FR2100712A1 (fr)	1972-03-24
CH563330A5 (fr)	1975-06-30
GB1288174A (fr)	1972-09-06
US3657327A (en)	1972-04-18
JPS5523825B1 (fr)	1980-06-25
PH9218A (en)	1975-07-10
SU384228A3 (fr)	1973-05-23
FI53308B (fr)	1977-12-30
SE377459B (fr)	1975-07-07
NL7107062A (fr)	1971-12-03
NO142499B (no)	1980-05-27
IL36860A (en)	1974-09-10
FR2100712B1 (fr)	1975-01-17
DE2126127A1 (de)	1971-12-09
OA03734A (fr)	1971-12-24
IL36860A0 (en)	1971-07-28
SE411345B (sv)	1979-12-17
DE2126127C2 (de)	1981-11-12
NO132194C (fr)	1975-10-15
ES391759A1 (es)	1973-06-16
SE387340B (sv)	1976-09-06
BE767926A (fr)	1971-12-01
GT197129402A (es)	1972-11-04
NO142499C (no)	1980-09-03

Legal Events

Date	Code	Title	Description
1991-07-15	PUP	Patent expired

Publication	Publication Date	Title
KR900001422B1 (ko)	1990-03-09	5-클로로-3-(2-테노일)-2-옥신돌-1-카복스아미드의 무수 결정성 나트륨 염
US3657327A (en)	1972-04-18	Prostaglandin salts of tris(hydroxymethyl)aminomethane
CA1097341A (fr)	1981-03-10	Methode de preparation d'une poudre cristalline sterile de cefozoline sodique qui se dissout rapidement pour administration parenterale
DK148022B (da)	1985-02-04	Fremgangsmaade til fremstilling af alfa-formen af krystallinsk natrium-o-formyl-cefamandol
US3703544A (en)	1972-11-21	Process for preparing the tris(hydroxymethyl)-aminomethane salt of pge2
US2765321A (en)	1956-10-02	Process of making crystalline warfarin sodium
DK142724B (da)	1981-01-05	Fremgangsmåde til fremstilling af fritstrømmende krystaller af tris (hydroxymethyl)aminomethan-saltet af prostaglandin E2.
SU657750A3 (ru)	1979-04-15	Способ получени кристаллической модификации натриевой соли 7 цианацетиламино-3-ацетоксиметил3-цефем-4-карбоновой кислоты
FI60703C (fi)	1982-03-10	Friflytande kristaller av foereningarnas pge2 och pgf2 alfa salter anvaendbara foer foedelsekontroll i daeggdjur
US3886203A (en)	1975-05-27	3-Hydroxyacyl aminomethyl-5-acylamino-2,4,6-triiodobenzoic acid salts as x-ray contrast agents
SU925251A3 (ru)	1982-04-30	Способ получени кристаллической формы D-конфигурации полуторной натриевой соли 7 @ -/ @ -карбокси- @ -(п-оксифенил) ацетамидо/-7 @ -метокси-3-(1-метилтетразол-5-ил)-тиометил-1-оксадетиа-3-цефем-4-карбоновой кислоты
JPS6151596B2 (fr)	1986-11-10
US2659722A (en)	1953-11-17	Penicillin salts of aminoalkylhydroxybenzoates
GB1589317A (en)	1981-05-13	Freeze drying cephalothin sodium
Patterson et al.	1933	Stereochemistry of N-Phenylpyrroles. XXIX. 1 Preparation and Properties of oN-Carbazyl-and oN-(3-Nitrocarbazyl)-benzoic acid
US3109001A (en)	1963-10-29	X-ray diffraction pattern of crystalline
US2552696A (en)	1951-05-15	Separation of the optical isomers of certain x-ray contrast agents
US2883399A (en)	1959-04-21	Method of preparing l(+)-glutamine
US3002994A (en)	1961-10-03	Purification of salts of dialkyl esters of sulfosuccinic acid
NO132353B (fr)	1975-07-21
Corwin et al.	1948	Acylization of Pyrryl Carboxylic Esters1, 2
Raiziss et al.	1926	N-ACYL DERIVATIVES OF 3-AMINO-4-HYDROXY-PHENYLARSONIC ACID
JPS5822477B2 (ja)	1983-05-09	スチレンスルホンサンキンゾクエンノセイセイホウ
GB654495A (en)	1951-06-20	Process for the preparation of new derivatives of penicillin
US2250256A (en)	1941-07-22	Method of producing trimethylolnitromethane