GB1297962A - - Google Patents
Info
- Publication number
- GB1297962A GB1297962A GB1297962DA GB1297962A GB 1297962 A GB1297962 A GB 1297962A GB 1297962D A GB1297962D A GB 1297962DA GB 1297962 A GB1297962 A GB 1297962A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dien
- methoxy
- alkyl
- propadienyl
- compounds
- 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.)
- Expired
Links
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000001589 carboacyl group Chemical group 0.000 abstract 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 2
- 229910052987 metal hydride Inorganic materials 0.000 abstract 2
- 150000004681 metal hydrides Chemical class 0.000 abstract 2
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 abstract 1
- XTAPYCRSTRJHGZ-XNZCMHNBSA-N 3-[(8S,9S,13S,14S,17R)-3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-N,N-dimethylprop-2-yn-1-amine Chemical compound COC1=CC=2CC[C@H]3[C@@H]4CC[C@H]([C@@]4(C)CC[C@@H]3C=2C=C1)C#CCN(C)C XTAPYCRSTRJHGZ-XNZCMHNBSA-N 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 238000010511 deprotection reaction Methods 0.000 abstract 1
- -1 dimethylamino - 1 - propynyl Chemical group 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 230000001076 estrogenic effect Effects 0.000 abstract 1
- 230000007717 exclusion Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000007069 methylation reaction Methods 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 230000001072 progestational effect Effects 0.000 abstract 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 150000003431 steroids Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1297962 17α-Propadienyl steroids SANDOZ Ltd 14 Nov 1969 [25 Nov 1968] 55842/69 Heading C2U The invention comprises compounds of formula wherein R 1 is C 1-3 alkyl; R 2 is H, Me or C 2-4 alkanoyl; R 4 is H, OH or C 2-4 alkanoyloxy; and Z, embracing rings A and B and the substituents thereon, represents one of the groups Z1 to Z9 wherein R 5 is H, C 1-3 alkyl, C 5-7 cycloalkyl or C 2-4 alkanoyl; R 6 is H, 6α-Me or 7α-Me; R 7 is H or Me; and R 8 is H, Me, F or C1; with the exclusion of: (i) 3,16α,17#-trihydroxy-17α-propadienyl - 13# - alkylgona - 1,3,5(10) - trienes (unsubstituted at the 6- and 7-positions) and esters thereof (see Specification 1,229,262); (ii) 17α- propadienyl - 17# - hydroxyestra - 4,9 - dien - 3- one (see Specification 1,297,963); (iii) 17α-propadienyl - 17# - hydroxyestr - 4 - en - 3 - one (see Specification 1,297,964); and (iv) 3#-acetoxy- 17α - propadienylestr - 4 - en - 17# - ol (see Specification 1,297,964). Preparation of compounds Ih is by complex metal hydride reduction of corresponding compounds having in the 17α-position the group -[C#C-CH 2 -NRR<SP>1</SP>R<SP>11</SP>]<SP>+</SP>.Y<SP>-</SP> (where R, R<SP>1</SP>. and R<SP>11</SP> are each C 1-3 alkyl, or R is C 1-3 alkyl and NR<SP>1</SP>R<SP>11</SP> is pyrrolidino or piperidino, and Y is Cl, Br, I, OSO 2 Me or O-tosyl) and in the 17#- position a free hydroxyl group, followed when required by 3,16- and/or 17-esterification or 17- O-methylation. The starting material is optionally protected, e.g. as a 3-methoxy-#<SP>2,5(10)</SP>- compound, in which case a deprotection step must follow the metal hydride reduction. 3 - Methoxy - 17α - (3 - dimethylamino - 1- propynyl)estra - 1,3,5(10) - trien - 17# - ol and its methiodide are prepared from the corresponding 17α-ethynyl compound. 3 - Methoxy - 17α - propadienylestra - 2,5(10)- dien-17#-ol is prepared from 3-methoxyestra-2- 5(10) - dien - 17 - one via 3 - methoxy - 17α - (3, dimethylamino - 1 - propynyl)estra - 2,5(10)- dien-17#-ol and the methiodide thereof. Compounds Ih are said to possess estrogenic and progestational activities, and may be made up with carriers into pharmaceutical compositions for oral and parenteral administration. Reference has been directed by the Comptroller to Specification 1,222,886.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US77877768A | 1968-11-25 | 1968-11-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1297962A true GB1297962A (en) | 1972-11-29 |
Family
ID=25114361
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1297963D Expired GB1297963A (en) | 1968-11-25 | 1969-11-14 | |
GB1297962D Expired GB1297962A (en) | 1968-11-25 | 1969-11-14 | |
GB1297964D Expired GB1297964A (en) | 1968-11-25 | 1969-11-14 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1297963D Expired GB1297963A (en) | 1968-11-25 | 1969-11-14 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1297964D Expired GB1297964A (en) | 1968-11-25 | 1969-11-14 |
Country Status (21)
Country | Link |
---|---|
JP (1) | JPS4826005B1 (en) |
AT (1) | AT330966B (en) |
BE (1) | BE742137A (en) |
BR (1) | BR6914427D0 (en) |
CA (1) | CA958005A (en) |
CH (3) | CH580115A5 (en) |
CS (5) | CS150694B2 (en) |
DE (1) | DE1966922A1 (en) |
DK (1) | DK127107B (en) |
ES (2) | ES387606A1 (en) |
FI (4) | FI47349C (en) |
FR (1) | FR2024166B1 (en) |
GB (3) | GB1297963A (en) |
HU (1) | HU164121B (en) |
NL (1) | NL149815B (en) |
NO (1) | NO134058C (en) |
PL (5) | PL80336B1 (en) |
SE (2) | SE378605B (en) |
SU (3) | SU402209A3 (en) |
YU (1) | YU34534B (en) |
ZA (1) | ZA698233B (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH571537A5 (en) * | 1970-04-24 | 1976-01-15 | Sandoz Ag | |
CH558346A (en) * | 1971-06-17 | 1975-01-31 | Sandoz Ag | METHOD FOR PRODUCING NEW 3-OXIMINO-17 (ALPHA) -PROPADIENYL-SUBSTITUTED STEROIDS. |
JPS5196702U (en) * | 1975-01-31 | 1976-08-03 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3392166A (en) * | 1966-03-30 | 1968-07-09 | Syntex Corp | Androst-4-enes and estr-4-enes having a 17alpha-diethylenically unsaturated side chain |
US3385871A (en) * | 1965-12-15 | 1968-05-28 | Syntex Corp | Halogenated cyclopropyl and cyclopropenyl estratrienes and process for their preparation |
-
1969
- 1969-02-24 SU SU1617457A patent/SU402209A3/ru active
- 1969-11-13 CH CH208573A patent/CH580115A5/xx unknown
- 1969-11-13 CH CH1695569A patent/CH579101A5/xx not_active IP Right Cessation
- 1969-11-13 CH CH208473A patent/CH571538A5/xx not_active IP Right Cessation
- 1969-11-14 GB GB1297963D patent/GB1297963A/en not_active Expired
- 1969-11-14 NL NL696917209A patent/NL149815B/en not_active IP Right Cessation
- 1969-11-14 GB GB1297962D patent/GB1297962A/en not_active Expired
- 1969-11-14 GB GB1297964D patent/GB1297964A/en not_active Expired
- 1969-11-20 DK DK615769AA patent/DK127107B/en unknown
- 1969-11-20 YU YU2911/69A patent/YU34534B/en unknown
- 1969-11-21 FI FI693387A patent/FI47349C/en active
- 1969-11-21 DE DE19691966922 patent/DE1966922A1/en active Pending
- 1969-11-24 CS CS7196A patent/CS150694B2/cs unknown
- 1969-11-24 FR FR6940364A patent/FR2024166B1/fr not_active Expired
- 1969-11-24 BE BE742137D patent/BE742137A/xx unknown
- 1969-11-24 SE SE7301830A patent/SE378605B/xx unknown
- 1969-11-24 CS CS7194A patent/CS150692B2/cs unknown
- 1969-11-24 AT AT1096369A patent/AT330966B/en not_active IP Right Cessation
- 1969-11-24 NO NO4651/69A patent/NO134058C/no unknown
- 1969-11-24 PL PL1969137088A patent/PL80336B1/en unknown
- 1969-11-24 HU HUSA2027A patent/HU164121B/hu unknown
- 1969-11-24 PL PL1969156780A patent/PL82607B1/en unknown
- 1969-11-24 JP JP44093688A patent/JPS4826005B1/ja active Pending
- 1969-11-24 CS CS7195A patent/CS150693B2/cs unknown
- 1969-11-24 SU SU1615145A patent/SU390714A3/ru active
- 1969-11-24 PL PL1969156778A patent/PL82606B1/en unknown
- 1969-11-24 BR BR214427/69A patent/BR6914427D0/en unknown
- 1969-11-24 SU SU1380086A patent/SU390715A3/ru active
- 1969-11-24 CS CS7721A patent/CS150690B2/cs unknown
- 1969-11-24 PL PL1969156777A patent/PL82605B1/en unknown
- 1969-11-24 CA CA068,167A patent/CA958005A/en not_active Expired
- 1969-11-24 SE SE16102/69A patent/SE369076B/xx unknown
- 1969-11-24 PL PL1969156783A patent/PL82690B1/en unknown
- 1969-11-24 CS CS7193A patent/CS150691B2/cs unknown
-
1970
- 1970-11-25 ZA ZA698233A patent/ZA698233B/en unknown
-
1971
- 1971-01-26 ES ES0387606A patent/ES387606A1/en not_active Expired
- 1971-01-26 ES ES0387605A patent/ES387605A1/en not_active Expired
-
1972
- 1972-08-23 FI FI722332A patent/FI47350C/en active
- 1972-08-23 FI FI722331A patent/FI48347C/en active
-
1973
- 1973-04-18 FI FI731256A patent/FI48583C/en active
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
PCNP | Patent ceased through non-payment of renewal fee |