DE1643036B2 - Neue 11 beta-halogensteroide, diese enthaltende arzneimittel sowie verfahren zu ihrer herstellung - Google Patents
Neue 11 beta-halogensteroide, diese enthaltende arzneimittel sowie verfahren zu ihrer herstellungInfo
- Publication number
- DE1643036B2 DE1643036B2 DE1967SC041166 DESC041166A DE1643036B2 DE 1643036 B2 DE1643036 B2 DE 1643036B2 DE 1967SC041166 DE1967SC041166 DE 1967SC041166 DE SC041166 A DESC041166 A DE SC041166A DE 1643036 B2 DE1643036 B2 DE 1643036B2
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- dione
- pregnadiene
- acid
- fluoro
- Prior art date
- 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.)
- Granted
Links
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- 239000000243 solution Substances 0.000 description 34
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- 150000002367 halogens Chemical class 0.000 description 20
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- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 230000023852 carbohydrate metabolic process Effects 0.000 description 1
- 235000021256 carbohydrate metabolism Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
- 229960005091 chloramphenicol Drugs 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012154 double-distilled water Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003221 ear drop Substances 0.000 description 1
- 229940047652 ear drops Drugs 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical compound ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000000344 gluconeogenetic effect Effects 0.000 description 1
- 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 1
- 229960002449 glycine Drugs 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
- 229940096919 glycogen Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 239000007923 nasal drop Substances 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002304 perfume Substances 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
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229940020414 potassium triiodide Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 201000004700 rosacea Diseases 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000000434 stratum corneum Anatomy 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-M succinate(1-) Chemical compound OC(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-M 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- RXPRRQLKFXBCSJ-GIVPXCGWSA-N vincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-GIVPXCGWSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229940045860 white wax Drugs 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1967SC041166 DE1643036B2 (de) | 1967-08-16 | 1967-08-16 | Neue 11 beta-halogensteroide, diese enthaltende arzneimittel sowie verfahren zu ihrer herstellung |
| CS5374A CS166686B2 (OSRAM) | 1967-08-16 | 1968-07-23 | |
| DK386468AA DK121082B (da) | 1967-08-16 | 1968-08-09 | Analogifremgangsmåde til fremstilling af 6α-fluor-9α, 11β-dihalogen-16α-methyl-1,4-pregnadien-21-ol-3,20-dioner eller estere heraf. |
| AT788568A AT280501B (de) | 1967-08-16 | 1968-08-12 | Verfahren zur Herstellung von neuen 11-Halogensteroiden |
| GB38617/68A GB1240719A (en) | 1967-08-16 | 1968-08-13 | New 11-halogenosteroids |
| ES357225A ES357225A1 (es) | 1967-08-16 | 1968-08-13 | Procedimiento de preparacion de nuevos 11-esteroides halo- genados. |
| IE994/68A IE32269B1 (en) | 1967-08-16 | 1968-08-13 | New 11-halogenosteroids |
| SE11006/68A SE339827B (OSRAM) | 1967-08-16 | 1968-08-15 | |
| US753034A US3609171A (en) | 1967-08-16 | 1968-08-15 | 11-halogen-substituted steroids |
| NL6811753.A NL161766C (nl) | 1967-08-16 | 1968-08-16 | Werkwijze ter bereiding van 3-oxo-6,9,11-trihalogeen- -delta 1,4 pregnadienen, alsmede werkwijze ter vervaar- diging van een geneesmiddel met ontstekingsremmende werking. |
| FI682324A FI45444C (fi) | 1967-08-16 | 1968-08-16 | Menetelmä tulehdusta estävien 6alfa-fluori-9alfa,11beta-dihalogeeni-16 alfa-metyyli-1,4-pregnadieeni-3,20-dionijohdannaisten valmistamiseksi |
| FR1601117D FR1601117A (OSRAM) | 1967-08-16 | 1968-08-16 | |
| BE719577D BE719577A (OSRAM) | 1967-08-16 | 1968-08-16 | |
| FR173683A FR8096M (OSRAM) | 1967-08-16 | 1968-11-14 | |
| US00173638A US3743741A (en) | 1967-08-16 | 1971-08-20 | Pharmaceutical composition based on 11-halogen substituted steroids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1967SC041166 DE1643036B2 (de) | 1967-08-16 | 1967-08-16 | Neue 11 beta-halogensteroide, diese enthaltende arzneimittel sowie verfahren zu ihrer herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1643036A1 DE1643036A1 (de) | 1971-04-15 |
| DE1643036B2 true DE1643036B2 (de) | 1976-04-15 |
Family
ID=7436074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1967SC041166 Granted DE1643036B2 (de) | 1967-08-16 | 1967-08-16 | Neue 11 beta-halogensteroide, diese enthaltende arzneimittel sowie verfahren zu ihrer herstellung |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US3609171A (OSRAM) |
| AT (1) | AT280501B (OSRAM) |
| BE (1) | BE719577A (OSRAM) |
| CS (1) | CS166686B2 (OSRAM) |
| DE (1) | DE1643036B2 (OSRAM) |
| DK (1) | DK121082B (OSRAM) |
| ES (1) | ES357225A1 (OSRAM) |
| FI (1) | FI45444C (OSRAM) |
| FR (2) | FR1601117A (OSRAM) |
| GB (1) | GB1240719A (OSRAM) |
| IE (1) | IE32269B1 (OSRAM) |
| NL (1) | NL161766C (OSRAM) |
| SE (1) | SE339827B (OSRAM) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1643036B2 (de) * | 1967-08-16 | 1976-04-15 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue 11 beta-halogensteroide, diese enthaltende arzneimittel sowie verfahren zu ihrer herstellung |
| US3933799A (en) * | 1969-01-29 | 1976-01-20 | Glaxo Laboratories Limited | 11β-Halo-9,12-unsubstituted-C19 -steroids |
| DE2064859C3 (de) * | 1970-12-30 | 1980-05-22 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue 6 a -Fluor-16 a , 18dimethyl-l,4-pregnadien-3,20-dion Derivate, Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel |
| US4304765A (en) * | 1980-10-14 | 1981-12-08 | Alza Corporation | Ocular insert housing steroid in two different therapeutic forms |
| US4432964A (en) * | 1981-08-24 | 1984-02-21 | Alza Corporation | Topical composition containing steroid in two forms released independently from polymeric carrier |
| US4478818A (en) * | 1982-12-27 | 1984-10-23 | Alza Corporation | Ocular preparation housing steroid in two different therapeutic forms |
| CA1310009C (en) * | 1984-03-28 | 1992-11-10 | John Mark Braughler | Ester prodrugs of steroids |
| US5707984A (en) * | 1995-12-08 | 1998-01-13 | G. D. Searle & Co. | Steroid nitrite/nitrate ester derivatives useful as anti-inflammatory drugs |
| US5792758A (en) * | 1995-12-08 | 1998-08-11 | G. D. Searle & Co. | Steroid nitrite ester derivatives useful as anti-inflammatory drugs |
| US5824669A (en) * | 1996-03-22 | 1998-10-20 | Nitromed, Inc. | Nitrosated and nitrosylated compounds and compositions and their use for treating respiratory disorders |
| US5837698A (en) * | 1996-05-02 | 1998-11-17 | G. D. Searle & Co. | Steroid nitrite and nitrate ester derivatives useful as anti-inflammatory drugs |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3426128A (en) * | 1961-02-22 | 1969-02-04 | Schering Ag | Delta**1,4-16alpha-methyl steroids |
| US3415855A (en) * | 1966-05-27 | 1968-12-10 | Schering Corp | Trichloro pregnadienes and esters thereof |
| US3422193A (en) * | 1966-08-11 | 1969-01-14 | Schering Corp | 17-mono esters of corticoids |
| DE1643036B2 (de) * | 1967-08-16 | 1976-04-15 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue 11 beta-halogensteroide, diese enthaltende arzneimittel sowie verfahren zu ihrer herstellung |
| US3501513A (en) * | 1968-02-29 | 1970-03-17 | Syntex Corp | Preparation of 17-desoxy steroids from corresponding 17alpha,21-dihydroxy - 20 - oxo steroids and 21-esters thereof |
-
1967
- 1967-08-16 DE DE1967SC041166 patent/DE1643036B2/de active Granted
-
1968
- 1968-07-23 CS CS5374A patent/CS166686B2/cs unknown
- 1968-08-09 DK DK386468AA patent/DK121082B/da unknown
- 1968-08-12 AT AT788568A patent/AT280501B/de not_active IP Right Cessation
- 1968-08-13 IE IE994/68A patent/IE32269B1/xx unknown
- 1968-08-13 ES ES357225A patent/ES357225A1/es not_active Expired
- 1968-08-13 GB GB38617/68A patent/GB1240719A/en not_active Expired
- 1968-08-15 SE SE11006/68A patent/SE339827B/xx unknown
- 1968-08-15 US US753034A patent/US3609171A/en not_active Expired - Lifetime
- 1968-08-16 FR FR1601117D patent/FR1601117A/fr not_active Expired
- 1968-08-16 FI FI682324A patent/FI45444C/fi active
- 1968-08-16 BE BE719577D patent/BE719577A/xx unknown
- 1968-08-16 NL NL6811753.A patent/NL161766C/xx not_active IP Right Cessation
- 1968-11-14 FR FR173683A patent/FR8096M/fr not_active Expired
-
1971
- 1971-08-20 US US00173638A patent/US3743741A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR8096M (OSRAM) | 1970-07-20 |
| BE719577A (OSRAM) | 1969-02-17 |
| NL6811753A (OSRAM) | 1969-02-18 |
| IE32269L (en) | 1969-02-16 |
| DE1643036A1 (de) | 1971-04-15 |
| GB1240719A (en) | 1971-07-28 |
| SE339827B (OSRAM) | 1971-10-25 |
| FI45444C (fi) | 1972-06-12 |
| NL161766B (nl) | 1979-10-15 |
| FI45444B (OSRAM) | 1972-02-29 |
| CS166686B2 (OSRAM) | 1976-03-29 |
| US3743741A (en) | 1973-07-03 |
| FR1601117A (OSRAM) | 1970-08-10 |
| DK121082B (da) | 1971-09-06 |
| NL161766C (nl) | 1980-03-17 |
| ES357225A1 (es) | 1970-03-01 |
| IE32269B1 (en) | 1973-05-30 |
| AT280501B (de) | 1970-04-10 |
| US3609171A (en) | 1971-09-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8320 | Willingness to grant licences declared (paragraph 23) |